Реакция #64372

Уравнение реакции

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

phosphorous acid

water

isopropanol

→

dibenzyl ether

Условия реакции

Обработка

1. 1
   Температураwas refluxed overnight
2. 2
   ДругоеThe solvent was evaporated on a rotary evaporator
3. 3
   Промывкаwashed successively with 10% hydrochloric acid, brine, and 5% sodium bicarbonate
4. 4
   СушкаThe organic layer was dried (magnesium sulfate)
5. 5
   Другоеthe solvent was evaporated

Методика

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.

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