Sulfuryl chloride → Ethyl 2-chloro-3-oxo-4-phenylbutyrate

HRID 1173779

Reaction equation

HRID 1173779 reaction equation
[O:1]=[C:2]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].S(Cl)([Cl:19])(=O)=O>C(Cl)Cl>[Cl:19][CH:3]([C:2](=[O:1])[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 225855Ethyl 3-oxo-4-phenylbutanoate

Product 1

HCID 11601176Ethyl 2-chloro-3-oxo-4-phenylbutyrateYield 86.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Ethyl 3-oxo-4-phenylbutyrate (4.8 g, 23 mmol) and methylene chloride (48 ml) were mixed, and sulfuryl chloride (3.1 g, 1 equivalent) was gradually added thereto dropwise. After the addition, the mixture was stirred at 20° C. for 1 hour. The reaction mixture was concentrated under reduced pressure, and saturated aqueous solution of sodium hydrogencarbonate (10 ml) was added, and extraction was carried out with ethyl acetate (20 ml). The solvent was evaporated away under reduced pressure and drying was carried out in vacuum to obtain the title compound as a yellow oil (4.8 g, yield: 86%).

Workup

  1. additionAfter the addition
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and saturated aqueous solution of sodium hydrogencarbonate (10 ml)
  3. additionwas added
  4. extractionextraction
  5. customThe solvent was evaporated away under reduced pressure
  6. customdrying

Sources & evidence

ORD record
ord-e6baa6b5b8594ff7abbfbb4adeb29779
Source dataset
uspto-grants-2010_11
Patent number
US07834190B2

Linked notes

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