Acetyl chloride → HCID 178501740, compound

HRID 1274963Notes

Reaction equation

HRID 1274963 reaction equation
[Cl:1][CH:2]([F:10])[C:3](=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].C([O:16][N:17]=O)CC(C)C.C(Cl)(=O)C.C(=O)(O)[O-].[Na+]>ClCCl.O>[Cl:1][CH:2]([F:10])[C:3](=[O:9])[C:4](=[N:17][OH:16])[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8053Isoamyl NitriteHCID 516892Sodium BicarbonateHCID 22118583HCID 22118583, compound

Product 1

HCID 178501740HCID 178501740, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-chloro-4-fluoro-3-oxobutyrate (31 g) and isopentylnitrite (25.8 ml) in dichloromethane (120 ml) was added dropwise acetylchloride (13 ml) under ice-cooling with stirring and the mixture was stirred for 3 hours at 5° C. to 10° C. The resulting solution was poured into water (300 ml) and adjusted to pH 3.0 with saturated aqueous sodium bicarbonate. The separated organic phase was washed with water (300 ml) and dried with magnesium sulfate and evaporated in vacuo to give methyl 4-chloro-4-fluoro-2-(hydroxyimino)-3-oxobutyrate.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 3 hours at 5° C. to 10° C
  3. washThe separated organic phase was washed with water (300 ml)
  4. dry with materialdried with magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-703d1bb5391b40f5a9b3c84234edf953
Source dataset
uspto-grants-2000_12
Patent number
US06159961

Reaction notes

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