Journal article

alpha-Hydroxymethylen-verlängerte Aldehyde durch schonende Reduktion von Cyanhydrinen

The OH group in cyanohydrins RR1C(OH)CN [R = Me2CH, R1 = H; R = R1 = Me; RR1 = (CH2)4, (CH2)5] was protected with EtOCH:CH2 to give RR1C(CN)OCHMeOEt, which were then reduced by NaAlH2(OCH2CH2OMe)2 to RR1C(CHO)OCHMeOEt (I) (53-70%), which were hydrolyzed with dil. acid to RR1C(OH)CHO (these compds. dimerize readily). I reacted with Ph3P+MeBr- and BuLi to give RR1C(CH:CH)OCHMeOEt and with LiAlH4 to give RR1C(CH2OH)OCHMeOEt. Reaction of PhCH(CN)OCHMeOEt with PhMgBr, followed by hydrolysis gave benzoin, and redn. with LiAlH4 in the presence of BzCl gave PhCH(OH)CH2NHBz. [on SciFinder (R)]


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