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

HRID 1659763Notes

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>O>[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

Conditions

Temperature: 40 °C

Procedure

A mixture 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 hours. After adding water (200 ml.) to the resultant solution, the mixture was extracted with methylene chloride. The extract was washed with water, a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate, and then concentrated in vacuo to give ethyl 2-(2-benzoyloxyethoxyimino)-4-chloro-3-oxobutyrate (syn isomer) (29 g.).

Workup

extractionthe mixture was extracted with methylene chloride
washThe extract was washed with water
dry with materiala saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-3a4690adc1b1443b8c7d71c4f05feeab
Source dataset: uspto-grants-1981_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04304770

Reaction notes

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