反应详情

To 56.3 g. of oxalyl chloride in 300 ml. of dry methylene chloride cooled to -60° C. and under a nitrogen atmosphere was added dropwise 74.81 g. of dimethylsulfoxide in 100 ml. of dry methylene chloride. After 15 minutes 92.0 g. of 3-(S)-methyl-5-(t-butyldimethylsilyloxy)-1-pentanol in 250 ml. of the same solvent was added dropwise. After 30 minutes 206.1 g. of triethylamine was added to -60° C. followed by the removal of the cooling bath. The reaction was stirred at room temperature for 1.5 hours, and was then poured into water and extracted with methylene chloride. The extracts were washed with 2.5% hydrochloric, a saturated sodium bicarbonate solution, water and a brine solution, and then dried over magnesium sulfate. The solvent was removed and the residue dissolved in ether and rewashed and dried as before. Removal of the ether gave 90.9 g. of the desired product.

1. additionwas added dropwise 74.81 g
2. additionof the same solvent was added dropwise
3. waitAfter 30 minutes 206.1 g
4. customfollowed by the removal of the cooling bath
5. additionwas then poured into water
6. extractionextracted with methylene chloride
7. washThe extracts were washed with 2.5% hydrochloric
8. dry with materiala saturated sodium bicarbonate solution, water and a brine solution, and then dried over magnesium sulfate
9. customThe solvent was removed
10. dissolutionthe residue dissolved in ether
11. customdried as before
12. customRemoval of the ether
13. customgave 90.9 g