Dichloromethane → Methyl 4-chloro-3-oxopentanoate

HRID 58217

Reaction equation

HRID 58217 reaction equation
[O:1]=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5].C(Cl)[Cl:11]>>[Cl:11][CH:8]([CH3:9])[C:2](=[O:1])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 121699Methyl 3-oxovalerate

Product 1

HCID 22068615Methyl 4-chloro-3-oxopentanoate

Procedure

To a solution of 3-oxopentanoic acid, methyl ester (Aldrich, 26.0 mL, 207.2 mmol) in methylene chloride (300 mL) was added in portions, N,N,N-trimethyl(phenyl) methanaminium dichloroiodanuide (75.71 g, 217.5 mmol). The reaction mixture was stirred at room temperature (rt) for 2 h, then washed with saturated sodium thiosulfate, brine, dried over magnesium sulfate and concentrated. The crude product was used directly in next step (23 g, 67.4%).

Workup

  1. washwashed with saturated sodium thiosulfate, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1b9a8e6ed9864abbb2720e1815947720
Source dataset
uspto-grants-2016_09
Patent number
US09434746B2

Linked notes

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