Potassium tert-butoxide → HCID 136436908, compound

Participants

Reaction Steps

Potassium t-butoxide (290 mg, 2.60 mmol) was added to a stirred solution of the title compound of Example 20 (239 mg, 0.43 mmol) in propan-2-ol (7 ml) under nitrogen and the reaction mixture heated under reflux for 48 hours, then allowed to cool. The resulting mixture was evaporated under reduced pressure and the residue partitioned between water (20 ml) and ethyl acetate (20 ml). The phases were separated, the aqueous phase extracted with ethyl acetate and the combined organic solutions dried (MgSO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, using an elution gradient of dichloromethane: methanol (100:0 to 95:5), to afford the title compound (84 mg, 35%) as a foam. δ (CDCl3): 1.28 (3H, t), 1.56 (6H, 2×d), 2.28 (3H, s), 2.50 (4H, m), 3.04 (2H, q), 3.14 (4H, m), 5.68 (3H, m), 7.09 (1H, d), 7.22 (1H, m), 7.62 (1H, m), 8.57 (1H, d), 8.62 (1H, s), 9.02 (1H, s), 10.68 (1H, s). LRMS: m/z 553 (M+1)+.

Provenance & Evidence