e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Chemistry Letters

A useful method for selective acylation of alcohols using 2, 2'-bipyridyl-6-yl carboxylate and cesium fluoride.

T Mukaiyama, FC Pai, M Onaka, K Narasaka

Index: Mukaiyama, Teruaki; Pai, Fong-Chang; Onaka, Makoto; Narasaka, Koichi Chemistry Letters, 1980 , p. 563 - 566

Full Text: HTML

Citation Number: 26

Abstract

Primary and secondary alcohols are acylated under mild conditions by the use of 2, 2′- bipyridyl-6-yl carboxylates and cesium fluoride. Furthermore, the reaction is successfully applied to selective acylation of a primary carbinol group of diols containing primary and secondary carbinol groups or exclusive O-acylation of aromatic amino alcohols.

4-Hydroxybenzyl alcohol Structure

4-Hydroxybenzyl...

2,2'-bipyridyl-6-yl acetate Structure

2,2'-bipyridyl-...

~72%

Benzenemethanol,4-(acetyloxy)- Structure

Benzenemethanol...

acetic acid 4-acetoxy-benzyl ester Structure

acetic acid 4-a...

Detail

Geraniol Structure

2,2'-bipyridyl-6-yl hexanoate Structure

2,2'-bipyridyl-...

~0%

GERANYL CAPROATE Structure

GERANYL CAPROATE

6-pyridin-2-yl-1H-pyridin-2-one Structure

6-pyridin-2-yl-...

Geraniol Structure

[2,2'-bipyridin]-6-yl 2-phenylacetate Structure

[2,2'-bipyridin...

~0%

Geranyl Phenylacetate Structure

Geranyl Phenyla...

6-pyridin-2-yl-1H-pyridin-2-one Structure

6-pyridin-2-yl-...

[2,2'-bipyridin]-6-yl 2-phenylacetate Structure

[2,2'-bipyridin...

Isopropanol Structure

~0%

isopropyl phenyl acetate Structure

isopropyl pheny...

6-pyridin-2-yl-1H-pyridin-2-one Structure

6-pyridin-2-yl-...

2,2'-bipyridyl-6-yl hexanoate Structure

2,2'-bipyridyl-...

Benzyl alcohol Structure

~0%

Benzyl Hexanoate Structure

Benzyl Hexanoate

6-pyridin-2-yl-1H-pyridin-2-one Structure

6-pyridin-2-yl-...

Geraniol Structure

2,2'-bipyridyl-6-yl acetate Structure

2,2'-bipyridyl-...

~0%

acetic acid geranyl ester Structure

acetic acid ger...

6-pyridin-2-yl-1H-pyridin-2-one Structure

6-pyridin-2-yl-...

[2,2'-bipyridin]-6-yl 2-phenylacetate Structure

[2,2'-bipyridin...

Benzyl alcohol Structure

~0%

3,3-Diphenylpropanoic acid Structure

3,3-Diphenylpro...

6-pyridin-2-yl-1H-pyridin-2-one Structure

6-pyridin-2-yl-...

nonane-1,5-diol Structure

nonane-1,5-diol

2,2'-bipyridyl-6-yl acetate Structure

2,2'-bipyridyl-...

~0%

1,5-diacetoxy-nonane Structure

1,5-diacetoxy-nonane

N/A Structure

Detail

4-Hydroxybenzyl alcohol Structure

4-Hydroxybenzyl...

2,2'-bipyridyl-6-yl acetate Structure

2,2'-bipyridyl-...

~0%

Benzenemethanol,4-(acetyloxy)- Structure

Benzenemethanol...

acetic acid 4-acetoxy-benzyl ester Structure

acetic acid 4-a...

Detail

4-Phenyl-2-butanol Structure

4-Phenyl-2-butanol

2,2'-bipyridyl-6-yl hexanoate Structure

2,2'-bipyridyl-...

~0%

4-phenylbutan-2-yl hexanoate Structure

4-phenylbutan-2...

6-pyridin-2-yl-1H-pyridin-2-one Structure

6-pyridin-2-yl-...

cholesterol Structure

[2,2'-bipyridin]-6-yl 2-phenylacetate Structure

[2,2'-bipyridin...

~0%

6-pyridin-2-yl-1H-pyridin-2-one Structure

6-pyridin-2-yl-...

cholesterol phenylacetate Structure

cholesterol phe...

2,2'-bipyridyl-6-yl acetate Structure

2,2'-bipyridyl-...

2-(4-Aminophenyl)ethanol Structure

2-(4-Aminopheny...

~0%

2-(4-aminophenyl)ethyl acetate Structure

2-(4-aminopheny...

2-(4-Acetamidophenyl)ethyl acetate Structure

2-(4-Acetamidop...

Detail

Tyramine Structure

2,2'-bipyridyl-6-yl acetate Structure

2,2'-bipyridyl-...

~0%

N-Acetyltyramine Structure

N-Acetyltyramine

6-pyridin-2-yl-1H-pyridin-2-one Structure

6-pyridin-2-yl-...

6-Aminohexan-1-ol Structure

6-Aminohexan-1-ol

2,2'-bipyridyl-6-yl acetate Structure

2,2'-bipyridyl-...

~0%

N-ACETYL-6-HYDROXY-N-HEXYLAMINE) Structure

N-ACETYL-6-HYDR...

6-pyridin-2-yl-1H-pyridin-2-one Structure

6-pyridin-2-yl-...

styrene glycol Structure

2,2'-bipyridyl-6-yl acetate Structure

2,2'-bipyridyl-...

~0%

N/A Structure

1,2-Ethanediol,1-phenyl-, 1,2-diacetate Structure

1,2-Ethanediol,...

Detail

4-Phenyl-2-butanol Structure

4-Phenyl-2-butanol

2,2'-bipyridyl-6-yl acetate Structure

2,2'-bipyridyl-...

~0%

4-phenyl-2-butyl acetate Structure

4-phenyl-2-buty...

6-pyridin-2-yl-1H-pyridin-2-one Structure

6-pyridin-2-yl-...

4-Aminophenol Structure

2,2'-bipyridyl-6-yl acetate Structure

2,2'-bipyridyl-...

~0%

(4-Aminophenyl)acetic acid Structure

(4-Aminophenyl)...

Acetaminophen Acetate (Acetaminophen Impurity) Structure

Acetaminophen A...

Detail

styrene glycol Structure

2,2'-bipyridyl-6-yl acetate Structure

2,2'-bipyridyl-...

~39%

N/A Structure

1,2-Ethanediol,1-phenyl-, 1,2-diacetate Structure

1,2-Ethanediol,...

Detail

4-Aminophenol Structure

2,2'-bipyridyl-6-yl acetate Structure

2,2'-bipyridyl-...

~86%

(4-Aminophenyl)acetic acid Structure

(4-Aminophenyl)...

Acetaminophen Acetate (Acetaminophen Impurity) Structure

Acetaminophen A...

Detail

Geraniol Structure

2,2'-bipyridyl-6-yl acetate Structure

2,2'-bipyridyl-...

~76%

acetic acid geranyl ester Structure

acetic acid ger...

6-pyridin-2-yl-1H-pyridin-2-one Structure

6-pyridin-2-yl-...

6-Aminohexan-1-ol Structure

6-Aminohexan-1-ol

2,2'-bipyridyl-6-yl acetate Structure

2,2'-bipyridyl-...

~60%

N-ACETYL-6-HYDROXY-N-HEXYLAMINE) Structure

N-ACETYL-6-HYDR...

6-pyridin-2-yl-1H-pyridin-2-one Structure

6-pyridin-2-yl-...

[2,2'-bipyridin]-6-yl 2-phenylacetate Structure

[2,2'-bipyridin...

Benzyl alcohol Structure

~83%

3,3-Diphenylpropanoic acid Structure

3,3-Diphenylpro...

6-pyridin-2-yl-1H-pyridin-2-one Structure

6-pyridin-2-yl-...

Tyramine Structure

2,2'-bipyridyl-6-yl acetate Structure

2,2'-bipyridyl-...

~56%

N-Acetyltyramine Structure

N-Acetyltyramine

6-pyridin-2-yl-1H-pyridin-2-one Structure

6-pyridin-2-yl-...

Geraniol Structure

[2,2'-bipyridin]-6-yl 2-phenylacetate Structure

[2,2'-bipyridin...

~85%

Geranyl Phenylacetate Structure

Geranyl Phenyla...

6-pyridin-2-yl-1H-pyridin-2-one Structure

6-pyridin-2-yl-...

2,2'-bipyridyl-6-yl hexanoate Structure

2,2'-bipyridyl-...

Benzyl alcohol Structure

~90%

Benzyl Hexanoate Structure

Benzyl Hexanoate

6-pyridin-2-yl-1H-pyridin-2-one Structure

6-pyridin-2-yl-...

[2,2'-bipyridin]-6-yl 2-phenylacetate Structure

[2,2'-bipyridin...

Isopropanol Structure

~85%

isopropyl phenyl acetate Structure

isopropyl pheny...

6-pyridin-2-yl-1H-pyridin-2-one Structure

6-pyridin-2-yl-...

4-Phenyl-2-butanol Structure

4-Phenyl-2-butanol

2,2'-bipyridyl-6-yl acetate Structure

2,2'-bipyridyl-...

~38%

4-phenyl-2-butyl acetate Structure

4-phenyl-2-buty...

6-pyridin-2-yl-1H-pyridin-2-one Structure

6-pyridin-2-yl-...

2,2'-bipyridyl-6-yl acetate Structure

2,2'-bipyridyl-...

2-(4-Aminophenyl)ethanol Structure

2-(4-Aminopheny...

~71%

2-(4-aminophenyl)ethyl acetate Structure

2-(4-aminopheny...

2-(4-Acetamidophenyl)ethyl acetate Structure

2-(4-Acetamidop...

Detail

Geraniol Structure

2,2'-bipyridyl-6-yl hexanoate Structure

2,2'-bipyridyl-...

~89%

GERANYL CAPROATE Structure

GERANYL CAPROATE

6-pyridin-2-yl-1H-pyridin-2-one Structure

6-pyridin-2-yl-...

Selective acylation of the phenolic hydroxyl of (hydroxyalky...

[Miyazawa, Toshifumi; Yamamoto, Masato; Danjo, Hiroshi Monatshefte fur Chemie, 2013 , vol. 144, # 9 p. 1351 - 1354]

Selective acylations of aminophenols and hydroxyalkylphenols...

[Paradisi, Mario Paglialunga; Zecchini, Giampiero Pagani; Torrini, Ines Tetrahedron Letters, 1986 , vol. 27, # 41 p. 5029 - 5032]

Novel para-substituted benzyl ethers for hydroxyl group prot...

[Jobron, Laurence; Hindsgaul, Ole Journal of the American Chemical Society, 1999 , vol. 121, # 24 p. 5835 - 5836]

Novel para-substituted benzyl ethers for hydroxyl group prot...

[Jobron, Laurence; Hindsgaul, Ole Journal of the American Chemical Society, 1999 , vol. 121, # 24 p. 5835 - 5836]

Indium Tri (isopropoxide)-Catalyzed Selective Meerwein–Ponnd...

[Lee, Jaeyoung; Ryu, Taekyu; Park, Sangjune; Lee, Phil Ho Journal of Organic Chemistry, 2012 , vol. 77, # 10 p. 4821 - 4825]