Ethyl Acetate → HCID 66652098, compound

Participants

Reaction Steps

Combine BuLi (0.1 ml, 1.6M, 0.16 mmol), methyltriphenylphosphonium bromide (0.063 g, 0.175 mmol) and tetrahydrofuran (1.0 ml) and stir 15 minutes. Add 8-Hydroxy-4-(4-hydroxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[a]naphthalene-6-carbaldehyde (0.012 g, 0.04 mmol) in tetrahydrofuran (1.0 ml) and stir 30 minutes. Take into ethyl acetate and wash with ammonium chloride solution solution, then brine. Dry over anhydrous sodium sulfate and concentrate to a residue which yields after separation on silica gel with 33% EtOAC/hexanes, the titled compound (0.006 g, 50%). 1H NMR (CD3OD) 7.15 (d, J=8.4, Hz, 2H), 7.04 (dd, J=11 and 6 Hz, 1H), 6.75 (m, 3H), 3.4 (m, 1H), 3.0 (m, 1H), 2.85 (m, 2H), 2.55(m, 1H) 2.2 (m, 1H), 1.6-1.2. MS m/z 305 (M−1).

Provenance & Evidence