Deprotection of N-sulfonyl nitrogen-heteroaromatics with tetrabutylammonium fluoride

A Yasuhara, T Sakamoto

Index: Yasuhara, Akito; Sakamoto, Takao Tetrahedron Letters, 1998 , vol. 39, # 7 p. 595 - 596

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Citation Number: 88

Abstract

A mixture of 2-phenyl-1-(phenylsulfonyl)indole (1a) (150 mg, 0.5 mmol), TBAF 1.0M solution in THF (0.5 ml, 0.5 mmol), and THF (20 ml) was refluxed for 1.5 hours. After cooling, the reaction mixture was evapolated in vacuo, and H 2 O (20 ml) was added to the residue. The mixture was extracted with Et 2 O (20 ml × 2), dried over MgSO 4 and evaporated in vacuo. The crude product was recystallized from acetonehexane to give colorless prisms (96 mg, 100%). mp 178 ...