Water → Oxazole, 2-(4-fluorophenyl)-4,5-dihydro-4,4-dimethyl-

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Reaction Steps

To a stirred solution of 2-amino-methylpropanol (0.378 mol, 33.64 gm) in 300 ml of methylene chloride at about 0° C. was added a solution of 4-fluorobenzoyl chloride (0.189 mol, 22.35 mL) in 100 mL of methylene chloride over about 0.5 hr. The mixture was allowed to warm to room temperature and stirred for about 3 hrs. The mixture was then poured into water and the layers were separated. The organic phase was washed with two portions of 10% HCl, one portion of saturated sodium chloride solution and dried over anhydrous MgSO4. Removal of the solvent in vacuo afforded a colorless solid which was stirred while SOCl2 (0.567 mol. 41 mL) was added dropwise over about 30 min. The resulting solution was stirred for about 0.5 hr, at which time diethyl ether was added while the solution was stirred rapidly. During this procedure, a colorless precipitate was produced. The slurry was filtered and the solid was washed with three 250 mL portions of diethyl ether. The solid was then dissolved in 300 mL of 3N KOH and the resulting solution was extracted with ethyl acetate. The organic extracts were washed with saturated aqueous NaCl solution and dried over MgSO4. Removal of the solvent in vacuo afforded 32 gm of the title compound of this Example 1A: 1HNMR (250 MHz., CDCl3) δ:8.00-7.91 (m, 2H), 7.10-7.02 (m, 2H), 4.11 (s, 2H), 1.39 (s, 6H).

Provenance & Evidence