Potassium Hydroxide → HCID 10074074, compound

Participants

Reaction Steps

To a solution of INTERMEDIATE 4a (428 mg) in tert-butanol (10 mL) was added crushed potassium hydroxide (129 mg, 2.5 eq) and the reaction was heated to reflux. After 90 minutes the reaction was cooled and diluted with dichloromethane (40 mL). The reaction was washed with water (30 mL) and the organic layer separated. The aqueous layer was neutralized with 2 N hydrochloric acid and washed with dichloromethane (2×25 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography, eluting 3% methanol in dichloromethane to yield COMPOUND 1 as a colorless foam (374.5 mg, 84%). 1H NMR (CD3OD) δ 1.06 (t, J=6.9 Hz, 3H), 1.20 (t, J=6.8 Hz, 3H), 3.15-3.40 (m, 6H), 3.545-3.54 (m, 2H), 3.57-3.67 (m, 4H), 4.44 (s, 2H), 5.39 (br s, 1H), 7.40 (d, J=8.4 Hz, 2H), 7.43-7.59 m, 6H), 7.82 (d, J=7.8 Hz, 3H), 7.93 (d, J=7.0 Hz, 1H), 8.22 (s, 1H).

Provenance & Evidence