3,4-Dimethoxybenzeneacetonitrile → (Z)-2-(3,4-dimethoxy-phenyl)-3-[2-(2-methoxy-ethoxymethoxy)-5-nitro-phenyl]-acrylonitrile

Participants

Reaction Steps

The hydroxyl group of 2-hydroxy-5-nitrobenzaldehyde (1.00 g) was protected by use of 2-methoxyethoxymethoxyl chloride (0.75 g) in accordance with (production process 1), to thereby produce an MEM form (1.10 g, yield: 65%). The resultant MEM form (510 mg) and 3,4-dimethoxybenzyl cyanide (354 mg) were subjected to condensation in accordance with process B of (production process 2), to thereby produce (Z)-2-(3,4-dimethoxy-phenyl)-3-[2-(2-methoxy-ethoxymethoxy)-5-nitro-phenyl]-acrylonitrile (330 mg, yield: 40%). The thus-produced (Z)-2-(3,4-dimethoxy-phenyl)-3-[2-(2-methoxy-ethoxymethoxy)-5-nitro-phenyl]-acrylonitrile (200 mg) was subjected to deprotection in accordance with (production process 3), to thereby produce the target product (87 mg, yield: 55%).

Provenance & Evidence