Tetrahydrofuran → HCID 178456442, compound

Participants

Reaction Steps

Sodium t-butoxide (0.15 g, 1.6 mmol) was added to a solution of Example 81D (70 mg, 0.78 mmol) in THF (1 mL). After 10 minutes, a solution of Example 125A (0.15 g, 0.4 mmol) in THF (1 mL) was added and the mixture stirred for 3 hours. The reaction was partitioned between dichloromethane with and saturated NaHCO3. The organic extract was washed with water and brine, dried with MgSO4, filtered, and concentrated. The residue was purified by chromatography (SiO2, hexane:EtOAc:MeOH:Et3N (8:8:1:0.2)) then recrystallized from EtOAc and hexanes to afford the title compound (0.1 g, 0.22 mmol, 56% yield). 1H NMR (300 MHz, Methanol-d4) δ ppm 0.94 (t, J=7.5 Hz, 3H), 1.27 (s, 6H), 1.46 (s, 9H), 1.70-1.82 (m, 2H), 3.96 (s, 5H), 4.26-4.33 (m, 2H), 6.77 (s, 1H), 7.18 (d, J=8.5 Hz, 1H), 7.61 (dd, J=8.5, 2.0 Hz, 1H), 7.77 (d, J=2.0 Hz, 1H); MS (DCI/NH3) m/z 456.1 (M+H)+.

Provenance & Evidence