Thionyl Chloride → HCID 11956971, compound

Participants

Reaction Steps

The title compound was prepared from 4-methoxybenzaldehyde (5.2 g, 38 mmol) by subjecting it to Grignard's reaction with 1-n-bromopropane by the method described in example 1(i) to give 1-(4-methoxyphenyl)-n-butanol of formula 3 (6.7 g, yield 98%). The secondary alcohol (5.55 g, 30 mmol) was subjected to Vilsmeier reaction with dimethyl formamide-phosphorous oxychloride as described in example 1 (ii) to furnish 2-formyl-1-(4-methoxyphenyl)-1-butene of formula 4 (4.0 g, 70%). The resulting aldehyde (3.8 g, 20 mmol) was subjected to Wittig reaction as described in example 1 (iii) followed by saponification to produce 5-(4-methoxyphenyl)-4-ethyl-2E,4E-pentadienoic acid of formula 6(3.0 g, 65%). The pentadienoic acid (1.0 g, 4.3 mmol) after acid chloride formation with thionyl chloride, and reaction with 4-hydroxypiperidine was purified by column chromatography on silica gel to give 5-(4-methoxyphenyl)-4-ethyl-2E,4E-pentadienoic acid piperidide of formula 1a (0.84 g, 60%).

Provenance & Evidence