Primary, secondary and tertiary alkyl borate esters can be prepared conveniently and in good yield by the transesterification of methyl borate with the appropriate alcohol. The high volatility of the methanol-methyl borate azeotrope provides a means of driving the reaction to completion. In the presence of one equivalent of acetic acid, sodium borohydride reacts smoothly with primary and secondary alcohols at room temperature in accordance with ...
[Campana, Araceli G.; Fuentes, Noelia; Gomez-Bengoa, Enrique; Mateo, Cristina; Oltra, J. Enrique; Echavarren, Antonio M.; Cuerva, Juan M. Journal of Organic Chemistry, 2007 , vol. 72, # 21 p. 8127 - 8130]