Réaction #65090

Équation de réaction

triethylamine

dimethyl sulfoxide

Oxalyl chloride

2-(5-hydroxy-3-pentynyl)cyclopropanecarboxylic acid methyl ester

sodium chloride

→

compound

Rendement 97.1%

2-(5-oxo-3-pentynyl)cyclopropanecarboxylic acid methyl ester

Rendement 97.1%

Solvants

dichloromethane

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe mixture was stirred for 30 minutes
2. 2
   TempératureThe temperature was raised to 0° C.
3. 3
   ExtractionThe product was extracted with dichloromethane
4. 4
   Séchagedried over anhydrous magnesium sulfate
5. 5
   Autrepurified by silica gel column chromatography
6. 6
   Autreto obtain the

Mode opératoire

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%).

Source