2-Amino-2-methyl-1-propanol → 2-(1-Chloro-2-methylpropan-2-yl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole

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Reaction Steps

2-(1,1-dimethyl-2-chloroethyl)-4,4-dimethyl-2-oxazoline was prepared as follows. Initially, N-(2-hydroxy-1,1-dimethylethyl)-3-chloropivalamide was prepared by adding dropwise, at room temperature, a solution of 3-chloropivaloyl chloride (1.0 eq., 56 g, 0.36 mol) in CHCl3 (100 mL) to a stirred mixture of 2-amino-2-methyl-1-propanol (2.0 eq., 64.4 g, 0.72 mol) in CHCl3 (300 mL) over a period of one (1) hour. This mixture was allowed to auto-reflux for twenty (20) minutes and was then stirred overnight. The whitish-yellow precipitate that formed was gravity filtered, and the resulting yellow-brown solution was concentrated and purified by vacuum distillation (140-150° C., 1 mm Hg). The resulting yellow oil (61 g, 81%) was pure N-(2-hydroxy-1,1-dimethylethyl)-3-chloropivalamide as evidenced by 1H NMR (CDCl3): δ1.13 (s, 6H, CH3, CH3), 1.30 (s, 6H, CH3, CH3), 2.2 (br s, 1H, OH), 3.3 (s, 2H, CH2,—Cl), 3.6 (s, 2CH2—OH), 5.78 (br s, 1H, NH).

Provenance & Evidence