[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:13]2[O:14][C:15]3[CH:21]=[C:20]([CH:22]([CH3:28])[C:23](OCC)=[O:24])[CH:19]=[CH:18][C:16]=3[N:17]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(OCC)(=O)C.Cl>CCOCC>[C:7]1([C:13]2[O:14][C:15]3[CH:21]=[C:20]([CH:22]([CH3:28])[CH2:23][OH:24])[CH:19]=[CH:18][C:16]=3[N:17]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1A solution of lithium aluminium hydride (~ 2 gm) in ether (50 ml) was slowly added to a solution of ethyl 2-(2-phenyl-6-benzoxazolyl)-propionate (5 g) in ether (40 ml). The mixture was heated under reflux for 1 hr., then ethyl acetate was slowly added until effervescence ceased. 6-N-Aqueous hydrochloric acid was then added and the ether layer was separated off and dried. Chromatography over silica gel yield pure 2-(2-phenyl-6-benzoxazolyl)-propanol, m.p. 98°C.
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