Practical procedure for the chemoselective reduction of esters by sodium borohydride. Effect of the slow addition of methanol.

K Soai, H Oyamada, M Takase, A Ookawa

Index: Soai; Oyamada; Takase; Ookawa Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 7 p. 1948 - 1953

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Citation Number: 107

Abstract

The effect of solvents on the reduction of esters was examined with readily available sodium borohydride which is known to be incapable of reducing such functional groups. In mixed solvents of t-butyl alcohol–methanol or tetrahydrofuran–methanol, various carboxylic esters and lactones were found to be reduced by sodium borohydride to the corresponding alcohols or diols in high yields. Slow addition of methanol to the refluxing mixture of ester ...