Water → 2-(4-Bromophenyl)-4,4-dimethyl-4,5-dihydrooxazole

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Reaction Conditions

Reaction Steps

2-(4-Bromophenyl)-4,4-dimethyl-1,3-oxazoline 1 was prepared as described in Example 4. To a stirred solution of 2-(4-bromophenyl)-4,4-dimethyl-1,3-oxazoline (1.5 g, 6 mM) in anhydrous THF (10 mL) at −78° C. was added slowly n-BuLi (384 mg, 6 mM) in hexane over the period of 20 min. After that the reaction mixture was stirred at −78° C. for another 30 min. To this stirred solution was added 3-hydroxybenzophenone (534 mg, 2.7 mM) dissolved in anhy. THF (10 mL) by dropwise at −78° C. and allowed to stir at room temperature overnight. To this reaction mixture was added 20 mL of water to quench the reaction and extracted with CH2Cl2 (3×50 mL) and the combined extract was dried over anhydrous Mg2SO4. The oily residue obtained on evaporation of the solvent was purified by silica gel column chromatography using hexane/EtOAc (1:1) mixture gave 3-{[4-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-hydroxy-phenyl-methyl}-phenol (2) as colorless crystalline solid. Yield: 0.855 g (85%). Mass: 374 (MH+), 372 (M-H).

Provenance & Evidence