Sulfuryl chloride → Ethyl 2-chloro-4-(2-methoxyethoxy)-3-oxobutanoate

HRID 2233890Notes

Reaction equation

HRID 2233890 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7](=[O:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].S(Cl)([Cl:18])(=O)=O>C(Cl)Cl.CCOC(C)=O>[Cl:18][CH:8]([C:7](=[O:14])[CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 2759572Butanoic acid, 4-(2-methoxyethoxy)-3-oxo-, ethyl ester2×

Product 1

HCID 86038328Ethyl 2-chloro-4-(2-methoxyethoxy)-3-oxobutanoateYield 70.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 4-(2-methoxyethoxy)-3-oxobutanoate (Intermediate 123) (0.5 g) was dissolved in anhydrous DCM (5 ml). Sulfuryl chloride (430 mg) was added dropwise at room temperature. The mixture was stirred for 6 h. The crude mixture was diluted with EtOAc (50 ml) and washed well with water and brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound as a light orange oil (414 mg).

Workup

  1. washwashed well with water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-339bde1c8c6b42179d06964ffd5121b5
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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