Water → 2-(4-Oxo-2-butynyl)cyclopropanecarboxylic acid methyl ester
Reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]([CH:11]1[CH2:13][CH:12]1[CH2:14][C:15]#[C:16][CH2:17][OH:18])=[O:10].C(N(CC)CC)C.O>ClCCl>[CH3:7][O:8][C:9]([CH:11]1[CH2:13][CH:12]1[CH2:14][C:15]#[C:16][CH:17]=[O:18])=[O:10]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -40 °C
Procedure
Oxalyl chloride (0.78 g, 6.2 mmol) was dissolved in dichloromethane (12 ml), and the solution was cooled to -40° C. A solution of dimethylsufloxide (1.0 g, 12.3 mmol) in dichloromethane (4 ml) was dropwise added thereto over a period of 10 minutes. Fifteen minutes later, a solution of 2-(4-hydroxy-2-butynyl)cyclopropanecarboxylic acid methyl ester (0.70 g, 4.1 mmol) in dichloromethane (5 ml) was dropwise added thereto over a period of 15 minutes. Forty minutes later, triethylamine (2.5 g, 25 mmol) was added thereto, and the temperature was raised to 0° C. Water was added thereto, and the product was extracted with dichloromethane, and the crude product thereby obtained was roughly separated by silica gel column chromatography to obtain 2-(4-oxo-2-butynyl)cyclopropanecarboxylic acid methyl ester (0.32 g).
Workup
- waitover a period of 15 minutes
- temperaturethe temperature was raised to 0° C
- extractionthe product was extracted with dichloromethane
- customthe crude product thereby obtained
- customwas roughly separated by silica gel column chromatography
Sources & evidence
- ORD record
- ord-ce9f3f0892a74cae951e30d9744af5b8
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05416231
Reaction notes
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