Oxalyl chloride → Butanoic acid, 4-chloro-4-oxo-, methyl ester

HRID 867399Notes

Reaction equation

HRID 867399 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][CH2:3][C:4]([O-])=[O:5].C(Cl)(=O)C([Cl:13])=O>CN(C)C=O.C(Cl)Cl>[C:1]([CH2:2][CH2:3][C:4]([Cl:13])=[O:5])([O:8][CH3:9])=[O:7]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 6930703Mono-Methyl Succinate

Product 1

HCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Mono-methyl succinate (1), wherein alk is methyl, was chlorinated with oxalyl chloride in dimethyl formamide and methylene chloride to afford 3-carbomethoxypropionyl chloride (2). Compound (2) was catalytically hydrogenated over palladium-charcoal catalyst in the presence of 2,6-lutidine to yield 3-carbomethoxypropionaldehyde (3) which was reacted with formylmethylene triphenylphosphorane under Wittig reaction conditions to obtain 5-carbomethoxy-2-pentanal (4). Compound 4 was epoxidized with aqueous hydrogen peroxide in the presence of 1N sodium bicarbonate to afford methyl-4,5-epoxy-6-oxohexanoate (5). Compound (5) was reacted with tridecyltriphenylphosphonium ylid to give methyl-4,5-epoxy-6(Z)-nonadecenoate (6).

Sources & evidence

ORD record
ord-500088371c8a4b538e1d9782950ca21b
Source dataset
uspto-grants-1988_10
Patent number
US04775662

Reaction notes

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