反应详情

A solution containing 84.6 g of N-methylmorpholine N-oxide, 1 g of osmium tetroxide, 230 ml of water and 115 ml of acetone was allowed to stir for 30 minutes at room temperature. To this stirred mixture was added, very slowly over at least 8 hours, a solution of 80 g of ethyl 3-cyclopentene-1-carboxylate in 115 ml of acetone. The stirred mixture was heated at 50° C. for 2 hours to complete the reaction (verified by TLC examination using ethyl acetate/hexane 70/30). Sodium bisulfite (~10 g) was added, the stirring continued for a further 15 minutes, and the mixture filtered through Celite. The pH of the filtrate was adjusted to 7 by the addition of 12 N sulfuric acid (37 ml), the acetone evaporated, the pH of the residual solution adjusted to 2 with 12 N sulfuric acid (13 ml) and the solution extracted with ethyl acetate (4×250 ml). Evaporation of the dried ethyl acetate solution gave 4-ethoxycarbonyl-1,2-cyclopentanediol.

1. additionTo this stirred mixture was added, very slowly over at least 8 hours
2. temperatureThe stirred mixture was heated at 50° C. for 2 hours
3. waitthe stirring continued for a further 15 minutes
4. filtrationthe mixture filtered through Celite
5. additionThe pH of the filtrate was adjusted to 7 by the addition of 12 N sulfuric acid (37 ml)
6. customthe acetone evaporated
7. extractionthe solution extracted with ethyl acetate (4×250 ml)
8. customEvaporation of the dried ethyl acetate solution