Hydrochloric Acid → 3-(2-Trifluoromethoxy-benzylsulfanyl)-5,5-dimethyl-4,5-dihydroisoxazole

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Reaction Conditions

Reaction Steps

2-(Trifluoromethoxy)benzyl alcohol (200 mg, 1.04 mmol), thiourea (100 mg, 1.31 mmol), aqueous hydrochloric acid (2M) (1.6 ml) and 1,4-dioxane (3 ml) were mixed and the mixture heated in a sealed vessel in the microwave at 140° C. for 10 minutes. Potassium carbonate (620 mg, 4.5 mmol) and 3-methanesulfonyl-5,5-dimethyl-4,5-dihydroisoxazole (220 mg, 1.24 mmol) were added and the mixture was stirred in an open vessel for 10 minutes. The mixture was heated in a sealed vessel in the microwave at 150° C. for 10 minutes. The mixture was diluted with water and extracted with ethyl acetate. The organic extract was washed with water, dried over magnesium sulfate and concentrated. The crude material was purified by chromatography on silica gel (eluent: ethyl acetate/hexane) to give the product as a white solid (50 mg, 15% yield). 1H-NMR (400 MHz, CDCl3): 1.41 (6H, s, Me), 2.78 (2H, s, CH2), 4.32 (2H, s, CH2), 7.2-7.4 (2H, m, CH), 7.57 (1H, m, CH).

Provenance & Evidence