Reaktion #64372

Reaktionsgleichung

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

phosphorous acid

water

isopropanol

→

dibenzyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed overnight
2. 2
   SonstigeThe solvent was evaporated on a rotary evaporator
3. 3
   Waschenwashed successively with 10% hydrochloric acid, brine, and 5% sodium bicarbonate
4. 4
   TrocknenThe organic layer was dried (magnesium sulfate)
5. 5
   Sonstigethe solvent was evaporated

Vorschrift

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.

Quelle