Reaktion #1264377

Reaktionsgleichung

3,5-bis-benzyloxy-4-oxiranylmethyl-benzoic acid tert-butyl ester

Et3N

K2CO3

→

title compound

Ausbeute 56.3%

4-Hydroxy-2-hydroxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester

Ausbeute 56.3%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered through Celite
2. 2
   EinengenThe filtrate was concentrated
3. 3
   Sonstigethe residue was purified by column chromatography (EtOAc/petroleum ether=1/3)

Vorschrift

A mixture of 3,5-bis-benzyloxy-4-oxiranylmethyl-benzoic acid tert-butyl ester (200e) (55 g, 0.12 mol), 10% Pd on Carbon (5 g), Et3N (15 g, 0.14 mol), and K2CO3 (20 g, 0.14 mol) in MeOH (250 mL) was stirred under 760 mmHg of H2 at room temperature for 4 hr. TLC (EtOAc/petroleum oil=1/2) showed the reaction was complete. The mixture was filtered through Celite. The filtrate was concentrated and the residue was purified by column chromatography (EtOAc/petroleum ether=1/3) to give the title compound (18 g, 55% yield) as an off-white solid.

Quelle