The Journal of Organic Chemistry

Reaction of enol ethers with formaldehyde and organoaluminum compounds

BB Snider, GB Phillips

Index: Snider, Barry B.; Phillips, Gary B. Journal of Organic Chemistry, 1983 , vol. 48, # 17 p. 2789 - 2792

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Citation Number: 12

Abstract

Results Reaction of ethyl propenyl ether, as a 78: 22 cis-trans mixture, with 2 equiv of paraformaldehyde and 2 equiv of Me& at 0" C in CH2Clz (Table I, run 1) gives a 65% yield of an 18: l mixture of threo-and erythro-3-ethoxy-2-methyl-1-butanol (2a) 5 (see eq 2). The relative stereo-erythro 2a chemistry of the isomers of 2a was proven by unambiguous synthesis of both isomers by sodium borohydride reduction of 3-ethoxy-2-methylbutal! ...