Water → 2-Oxobicyclo[4.1.0]heptane-1-acetic Acid Ethyl Ester
Reaction equation
[I-].[CH3:2][S+](C)(C)=O.[CH2:7]([O:9][C:10](=[O:19])[CH2:11][C:12]1[C:17](=[O:18])[CH2:16][CH2:15][CH2:14][CH:13]=1)[CH3:8].O>CS(C)=O>[CH2:7]([O:9][C:10](=[O:19])[CH2:11][C:12]12[CH2:2][CH:13]1[CH2:14][CH2:15][CH2:16][C:17]2=[O:18])[CH3:8]Participants
Procedure
Sodium hydride (18.1 mmol, 543 mg of an 80% dispersion in mineral oil) was washed with 2×5 mL of petroleum ether under nitrogen, then it was dried and trimethylsulfoxonium iodide (3.99 g, 18.1 mmol) was added to the flask followed by 21.6 mL dimethylsulfoxide added dropwise. Next, a solution of 6-oxo-1-cyclohexeneacetic acid ethyl ester (2.90 g, 17.3 mmol) was added dropwise as a solution in 4.5 mL of dimethylsulfoxide as the reaction mixture was cooled with a water bath. After the addition, the reaction mixture was stirred at room temperature for 1.5 hours then poured into 80 mL of cold water and extracted with 4×60 mL of ether. The extracts were combined, washed with 80 mL of brine, dried over magnesium sulfate and concentrated affording 2.4 g (13.2 mmol, 73% yield) of the title compound as a yellow oil.
Workup
- washSodium hydride (18.1 mmol, 543 mg of an 80% dispersion in mineral oil) was washed with 2×5 mL of petroleum ether under nitrogen
- customit was dried
- additionadded dropwise
- temperaturewas cooled with a water bath
- additionAfter the addition
- extractionextracted with 4×60 mL of ether
- washwashed with 80 mL of brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4a32c529c1764de2bbcb1aaa274536b7
- Source dataset
- uspto-grants-1989_12
- Patent number
- US04888431
Reaction notes
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