Sulfuryl chloride → Ethyl 2-(2-benzoyloxyethoxyimino)-4-chloro-3-oxobutyrate

HRID 1154112Notes

Reaction equation

HRID 1154112 reaction equation
[C:1]([O:9][CH2:10][CH2:11][O:12][N:13]=[C:14]([C:20](=[O:22])[CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:26])(=O)=O>C(O)(=O)C>[C:1]([O:9][CH2:10][CH2:11][O:12][N:13]=[C:14]([C:20](=[O:22])[CH2:21][Cl:26])[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 53765835Ethyl 2-(2-benzoyloxyethoxyimino)-3-oxobutyrate

Product 1

HCID 53906646Ethyl 2-(2-benzoyloxyethoxyimino)-4-chloro-3-oxobutyrateYield 93.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 15.7 g.), 2-bromoethyl benzoate (27.5 g.), potassium carbonate (20.7 g.), N,N-dimethylformamide (25 ml.) and ethyl acetate (25 ml.) was stirred at room temperature for 4 hrs. The reaction mixture was treated in a conventional manner to give ethyl 2-(2-benzoyloxyethoxyimino)-3-oxobutyrate (syn isomer, 28 g.). (2) A solution of ethyl 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-4d578a9b7e2b4538be350a33458f9c2d
Source dataset
uspto-grants-1984_12
Patent number
US04487767

Reaction notes

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