Réaction #64372

Équation de réaction

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

phosphorous acid

water

isopropanol

→

dibenzyl ether

Conditions de réaction

Traitement

1. 1
   Températurewas refluxed overnight
2. 2
   AutreThe solvent was evaporated on a rotary evaporator
3. 3
   Lavagewashed successively with 10% hydrochloric acid, brine, and 5% sodium bicarbonate
4. 4
   SéchageThe organic layer was dried (magnesium sulfate)
5. 5
   Autrethe solvent was evaporated

Mode opératoire

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.

Source