반응 #445542

반응 방정식

diisobutylaluminium hydride

lactone

(1S,5R,6R,7R)-6-[(1E)-(3S)-3-(tetrahydropyran-2-yloxy)-1-octen-5-ynyl]-7-(tetrahydropyran-2-yloxy)-2-oxabicyclo[3.3.0]-octan-3-one

isopropanol

water

→

title compound

수율 96.1%

(2RS,3aR,4R,5R,6aS)-4-[(1E)-(3S)-3-(tetrahydropyran-2-yloxy)-1-octen-5-ynyl]-2-hydroxy-5-(tetrahydropyran-2-yloxy)-perhydrocyclopenta[b]furan

수율 96.1%

용매

toluene

반응 조건

후처리

1. 1
   여과The precipitate is filtered off
2. 2
   세척washed with methylene chloride
3. 3
   건조the combined organic phases are dried over magnesium sulphate
4. 4
   농축concentrated

실험 절차

17.9 ml of a diisobutylaluminium hydride solution (20% in toluene) are added dropwise, under argon, to a solution of 4.3 g of the lactone prepared in Example (23f) in 84 ml of toluene cooled to -70° C. After 0.5 hour, 1.0 ml of isopropanol and 8.97 ml of water are added to the reaction mixture and the whole is stirred at room temperature for 2.5 hours. The precipitate is filtered off and washed with methylene chloride, and the combined organic phases are dried over magnesium sulphate and concentrated; 4.15 g of the title compound are obtained in the form of an oil.

출처