Sulfuryl chloride → 6-Benzyloxy-2-chloro-3-oxo-hexanoic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6](=[O:18])[CH2:7][CH2:8][CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2].S(Cl)([Cl:23])(=O)=O>ClCCl>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([Cl:23])[C:6](=[O:18])[CH2:7][CH2:8][CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 13.9 g of crude 6-Benzyloxy-3-oxo-hexanoic acid ethyl ester in 50 ml dichloromethane were added dropwise 4.3 ml sulfuryl chloride. The reaction mixture was stirred at 0° C. and then at room temperature for thirty minutes. The reaction mixture was poured on ice and extracted three times with portions of 150 ml dichloromethane. The combined organic layers were washed with water, dried over MgSO4 and then the solvent was evaporated in vacuo to obtain 14.9 g of crude 6-Benzyloxy-2-chloro-3-oxo-hexanoic acid ethyl ester as a yellow oil.
Workup
- waitat room temperature for thirty minutes
- additionThe reaction mixture was poured on ice
- extractionextracted three times with portions of 150 ml dichloromethane
- washThe combined organic layers were washed with water
- dry with materialdried over MgSO4
- customthe solvent was evaporated in vacuo
Sources & evidence
- ORD record
- ord-55c8732d41414349bb4df5ee2c9554f8
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709481B2
Reaction notes
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