Potassium Carbonate → HCID 59739616, compound

Participants

Reaction Steps

Thiourea (2.15 g, 28.21 mmol) was added to a solution of 1-bromo-2-butyne (2.47 ml, 28.21 mmol) in ethanol (69 ml) and the solution was heated under reflux for 1 hour 40 minutes. The mixture was allowed to cool to room temperature and 3-methanesulfonyl-5,5-dimethyl-4,5-dihydroisoxazole (5 g, 28.21 mmol) and potassium carbonate (4.28 g, 31.03 mmol) were added. The mixture was heated under reflux for 2 hours 35 minutes and allowed to cool to room temperature. The mixture was partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel (eluent: ethyl acetate/hexane) to give the product (3.085 g, 60% yield) as a pale yellow oil. 1H-NMR (400 MHz, CDCl3): 1.42 (6H, s, Me), 1.83 (3H, t, Me), 2.81 (2H, s, CH2), 3.77 (2H, q, CH2).

Provenance & Evidence