Aluminium lithium hydride → [2-(4-Methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxymethyl)-oxazol-4-yl]-methanol

Participants

Reaction Steps

5.3 g 2-(4-Methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxymethyl)-oxazole-4-carboxylic acid ethyl ester were dissolved in 100 ml tetrahydrofuran and cooled in an ice bath. 21.8 ml of a one molar solution of lithium aluminium hydride in tetrahydrofuran were added. The cooling bath was removed and the reaction mixture stirred at room temperature for thirty minutes. The reaction mixture was cooled in an ice bath again and sequentially added 6 ml water, 12 ml 15% NaOH and 18 ml water. After being stirred for one hour at room temperature the reaction mixture was filtered over a pad of celite and washed with ethyl acetate. The filtrate was dried over MgSO4 and the solvent was removed in vacuo and the residue purified by flash chromatography on silica gel (eluting with n-heptane:ethyl acetate=6:4=>9:1=>ethyl acetate) to obtain 3.0 g [2-(4-Methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxymethyl)-oxazol-4-yl]-methanol.

Provenance & Evidence