Reaktion #352091

Reaktionsgleichung

5-benzyloxy-1,4-benzodioxane-7-carboxylic acid ethyl ester

lithium aluminium hydride

ethyl acetate

sulfuric acid

→

title compound

5-Benzyloxy-7-hydroxymethyl-1,4-benzodioxane

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture is partitioned between diethyl ether and water
2. 2
   TrocknenThe organic phases are dried over sodium sulfate
3. 3
   Einengenconcentrated by evaporation

Vorschrift

A solution of 1.28 g of 5-benzyloxy-1,4-benzodioxane-7-carboxylic acid ethyl ester in 5 ml of tetrahydrofuran is added dropwise at room temperature to a solution of 110 mg of lithium aluminium hydride in 10 ml of tetrahydrofuran and the mixture is stirred at room temperature for a further 30 minutes. Then 0.22 ml of ethyl acetate, 1.5 ml of a mixture (water/tetrahydrofuran=1:1) and finally 2.25 ml of 2N sulfuric acid are added dropwise in succession. The reaction mixture is partitioned between diethyl ether and water. The organic phases are dried over sodium sulfate and concentrated by evaporation. The title compound is obtained from the residue by FC (240 g of silica gel, ethyl acetate/hexane=1:2): Rf (ethyl acetate-hexane=1:2)=0.18.

Quelle