Acetic Acid → Ethyl 2-(2-benzoyloxyethoxyimino)-4-chloro-3-oxobutyrate

HRID 27270Notes

Reaction equation

HRID 27270 reaction equation
[C:1]([O:9][CH2:10][CH2:11][O:12][N:13]=[C:14]([C:18](=[O:20])[CH3:19])[C:15]([O-:17])=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:24])(=O)=O.[C:26](O)(=O)[CH3:27]>>[C:1]([O:9][CH2:10][CH2:11][O:12][N:13]=[C:14]([C:18](=[O:20])[CH2:19][Cl:24])[C:15]([O:17][CH2:26][CH3:27])=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 24648Sulfuryl chlorideHCID 867371922-(2-Benzoyloxyethoxyimino)-3-oxobutyrate

Product 1

HCID 53906646Ethyl 2-(2-benzoyloxyethoxyimino)-4-chloro-3-oxobutyrate

Procedure

A solution of 2-(2-benzoyloxyethoxyimino)-3-oxobutyrate (syn isomer, 28 g.), sulfuryl chloride (13.5 g.) and acetic acid (30 ml.) was stirred at 40° C. for 10 minutes and at room temperature for 5.5 hrs. The reaction mixture was treated in a conventional manner to give ethyl 2-(2-benzoyloxyethoxyimino)-4-chloro-3-oxobutyrate (syn isomer, 29 g.).

Workup

  1. additionThe reaction mixture was treated in a conventional manner

Sources & evidence

ORD record
ord-543dacb9fc1340ff993e4c9130a635d3
Source dataset
uspto-grants-1980_09
Patent number
US04220761

Reaction notes

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