Dimethyl Sulfoxide → 2-(5-Oxo-3-pentynyl)cyclopropanecarboxylic acid methyl ester
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][C:13]([CH:15]1[CH2:17][CH:16]1[CH2:18][CH2:19][C:20]#[C:21][CH2:22][OH:23])=[O:14].C(N(CC)CC)C.[Cl-].[Na+]>ClCCl>[CH3:11][O:12][C:13]([CH:15]1[CH2:17][CH:16]1[CH2:18][CH2:19][C:20]#[C:21][CH:22]=[O:23])=[O:14]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -40 °C
Procedure
Oxalyl chloride (0.40 g, 3.1 mmol) was dissolved in dichloromethane, and the solution was cooled to -40° C. A solution of dimethyl sulfoxide (0.52 g, 6.2 mmol) in dichloromethane (2 ml) was added thereto over a period of 5 minutes, and the mixture was stirred for 20 minutes. A solution of 2-(5-hydroxy-3-pentynyl)cyclopropanecarboxylic acid methyl ester (0.37 g, 2 mmol) in dichloromethane (5 ml) was added thereto, and the mixture was stirred for 30 minutes. Then, triethylamine (1.7 ml, 12 mmol) was added thereto. The temperature was raised to 0° C., and a saturated sodium chloride aqueous solution was added thereto. The product was extracted with dichloromethane, dried over anhydrous magnesium sulfate and then purified by silica gel column chromatography to obtain the above identified compound (0.35 g, yield: 96%).
Workup
- stirringthe mixture was stirred for 30 minutes
- temperatureThe temperature was raised to 0° C.
- extractionThe product was extracted with dichloromethane
- dry with materialdried over anhydrous magnesium sulfate
- custompurified by silica gel column chromatography
- customto obtain the
Sources & evidence
- ORD record
- ord-4396e180818a44a9afcb702bc14349a3
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05416231
Reaction notes
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