Pyridine → HCID 22908396, compound

Participants

Reaction Steps

After 0.21 g of (RS)-3-(1-methyl-2-propenyl)-4-methylidenecyclopent-2-en-1-ol was dissolved in 5 ml of toluene, 0.14 ml of pyridine was added to the toluene solution. Under ice-water cooling, 70%(w/w) toluene solution containing 0.32 g of 2,2,3,3-tetramethylcyclopropanecarboxylic acid chloride was added dropwise to the mixed solution, and then stirred at an ambient temperature for six hours. The reaction solution was poured into ice-water and extracted with ethyl acetate. The ethyl acetate layer was washed successively with 5% aqueous hydrochloric acid and water, and vigorously stirred with 5% ammonia water for two hours. The ethyl acetate layer was then washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the obtained oily substance was subjected to silica gel column chromatography to yield 0.24 g of (RS)-3-(1-methyl-2-propenyl)-4-methylidenecyclopenten-2-yl 2,2,3,3-tetramethylcyclopropanecarboxylate (Compound No.12). Yield 62% nD23 1.5023

Provenance & Evidence