Dichloromethane → Methyl 2-chloro-4,4-dimethoxy-3-oxopentanoate

HRID 1948360Notes

Reaction equation

HRID 1948360 reaction equation
[CH3:1][O:2][C:3]([O:12][CH3:13])([CH3:11])[C:4](=[O:10])[CH2:5][C:6]([O:8][CH3:9])=[O:7].C(Cl)[Cl:15]>>[Cl:15][CH:5]([C:4](=[O:10])[C:3]([O:2][CH3:1])([O:12][CH3:13])[CH3:11])[C:6]([O:8][CH3:9])=[O:7]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 5076552Methyl 4,4-dimethoxy-3-oxopentanoate

Product 1

HCID 59208484Methyl 2-chloro-4,4-dimethoxy-3-oxopentanoate

Procedure

SO2Cl2 (2.2 ml, 27 mmol) was added slowly to a solution of 5.0 g (26 mmol) of methyl 4,4-dimethoxy-3-oxopentanoate in 30 ml CH2Cl2 cooled in an ice water bath. The solution was warmed to room temperature and stirred for 1 h. Solvent was removed and the residue was taken up in EtOAc, which was washed with water and brine. Drying (MgSO4) and removal of solvent gave 6.1 g of an oil. NMR: (CDCl3): 1.5 (s, 3H), 3.25 (2s, 6H), 4.8 (s, 3H), 5.3 (s, 1H).

Workup

  1. temperaturecooled in an ice water bath
  2. customSolvent was removed
  3. washwhich was washed with water and brine
  4. customDrying
  5. custom(MgSO4) and removal of solvent

Sources & evidence

ORD record
ord-91090372fce14ae09617144ab9b3b6dc
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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