Methyl Bromide → 2-(3-(Benzyloxy)phenyl)-2-methylpropanal

Participants

Reaction Steps

Commercially available (3-benzyloxy-phenyl)-acetonitrile (I) was converted to 2-(3-benzyloxy-phenyl)-2-methyl-propionitrile (II) using methyl bromide gas in NaOH/DMSO, followed by a reduction with DIBAL-H yielding 2-(3-benzyloxy-phenyl)-2-methylpropionaldehyde (III). Further reduction of III with NaBH4 afforded 2-(3-benzyloxy-phenyl)-2-methyl-propan-1-ol (IV). Wittig reactions of III with pentyltriphenylphosphonium bromide, trimethyl-4-phosphonocrotonate and trimethyl phosphonoacetate, produced 1-(1,1-dimethyl-hept-2-enyl)-3-phenethyl-benzene (V), 6-(3-benzyloxy-phenyl)-6-methyl-hepta-2,4-dienoic acid methyl ester (VIa), and 4-(3-benzyloxy-phenyl)-4-methyl-pent-2-enoic acid methyl ester (VIb) respectively (Scheme 1).

Provenance & Evidence