Sodium Methoxide → HCID 87366641, compound

Participants

Reaction Steps

Sodium methoxide (30%, ca 0.1 mL) was added dropwise to a stirred solution of benzoate 41 (209 mg, 0.168 mmol) in dry methanol (6 mL) and dichloromethane (2 mL) under argon. After 12 hrs the reaction mixture was partitioned between ether (50 mL) and 2M HCl (50 mL). The aqueous phase was re-extracted with ether (50 mL) and the combined ethereal extract washed with H2O (60 mL). After drying (MgSO4) and filtration the solvent was removed at reduced pressure to give the crude product that was purified by column chromatography on silica gel. Gradient elution with ethyl acetate/petroleum ether (30:70→50:50) afforded the title compound 42 (150 mg, 0.132 mmol, 79%) as a thin film; [α]D22 +61.3 (c 3.00, CH2Cl2); 1H NMR (300 MHz, CDCl3) δ 7.35-7.15 (m, 40H), 4.90-4.35 (m, 18H), 4.10-3.82 (m, 9H), 3.70-3.42 (m, 9H); 13C NMR (75 MHz, CDCl3) δ 139.2, 139.1, 139.0, 138.9, 138.4, 128.8, 128.7, 128.6, 128.5, 128.4, 128.2, 128.1, 128.0, 127.9, 99.4, 99.2, 79.5, 77.1, 77.0, 75.5, 75.2, 73.9, 73.8, 73.6, 73.5, 71.1, 71.0, 70.2, 69.7, 69.6, 69.5; HRMS-ESI (+ve) (Found: m/z 1154.5579 (MNH4+). C71H80NO14 requires m/z 1154.5624).

Provenance & Evidence