Thionyl Chloride → HCID 11956971, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[C:10](\[CH2:16][CH3:17])/[CH:11]=[CH:12]/[C:13]([OH:15])=O)=[CH:5][CH:4]=1.S(Cl)(Cl)=O.O[CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6](/[CH:9]=[C:10](\[CH2:16][CH3:17])/[CH:11]=[CH:12]/[C:13]([N:26]2[CH2:27][CH2:28][CH2:23][CH2:24][CH2:25]2)=[O:15])=[CH:7][CH:8]=1Participants
Procedure
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%).
Workup
- customwas purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-1f793cc6466145c99cc1e50de70e52d8
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08580752B2
Reaction notes
Loading…