Water → HCID 18989186, compound

Participants

Reaction Steps

A solution containing 5-(3-cyclopropyl-2-ethoxymethylene-1,3-dioxoprop-1-yl)-3,4-dimethoxybenzo[b]thiophene (0.59 g) and hydroxylamine hydrochloride (0.137 g) was stirred for 15 minutes in ethanol. Sodium acetate (anhydrous, 0.161 g) was added and the mixture stirred for 4 hours, before evaporation of the ethanol and addition of water. The mixture was extracted with ethyl acetate, dried (anhydrous magnesium sulphate) and evaporated in vacuo. The residue was purified by column chromatography on silica, eluting with ether/cyclohexane to yield 5-cyclopropyl-4-(3,4dimethoxybenzo[b]thien-5-oyl)isoxazole (compound 3, 0.24 g) as an oil, NMR δ1.20 (2H,m), 1.35 (2H,m), 2.80 (1H,m), 3.84 (3H,s), 4.00 (3H,s), 6.39 (1H,s), 7.40 (1H, d), 7.59 (1H, d), 8.29 (1H,s).

Provenance & Evidence