반응 #64372

반응 방정식

(2S-trans)-2,3-bis[(benzyloxy)methyl]cyclobutanone

phosphorous acid

water

isopropanol

→

dibenzyl ether

반응 조건

후처리

1. 1
   온도was refluxed overnight
2. 2
   기타The solvent was evaporated on a rotary evaporator
3. 3
   세척washed successively with 10% hydrochloric acid, brine, and 5% sodium bicarbonate
4. 4
   건조The organic layer was dried (magnesium sulfate)
5. 5
   기타the solvent was evaporated

실험 절차

A mixture of (2S-trans)-2,3-bis[(benzyloxy)methyl]cyclobutanone (0.25 g., 0.806 mmole), iridium tetrachloride (0.016 g., 0.0483 mmole), phosphorous acid (0.397 g., 4.84 mmole) and water (0.3 ml.) in isopropanol (3 ml.) was refluxed overnight. The solvent was evaporated on a rotary evaporator. The residue was taken up in ethyl acetate and washed successively with 10% hydrochloric acid, brine, and 5% sodium bicarbonate. The organic layer was dried (magnesium sulfate) and the solvent was evaporated to give [1S-(1α,2β,3β)]-3-hydroxy-1,2-cyclobutanedimethanol, dibenzyl ether; TLC (40% ethyl acetate/hexane) Rf =0.51.

출처