Hydrochloric Acid → HCID 68494361, compound

Participants

Reaction Conditions

Reaction Steps

Finely powdered sodium borohydride (3.38 g, 89.3 mmol) was covered with THF (40 mL) and ethanol (40 mL) and cooled to 0° C. 257 (13.95 g, 44.5 mmol) was dissolved in THF (120 mL) and added slowly over 2 h via dropping funnel. The reaction mixture was stirred for 4 h at 0° C. and then for 60 h at room temperature. Hydrochloric acid (2M, 45 mL) was added very carefully. The two layers were separated and the organic layer was concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2: 100 g, hexane/ethyl acetate 90:10) to give the title compound (8.83 g, 62%) as yellow solid. 1H NMR (270 MHz, CDCl3) δ 0.91 (3H, t, J 7.4, CH2CH3), 1.62-1.79 (1H, m, one of CHCH2CH3), 1.81-2.00 (1H, m, one of CHCH2CH3), 2.88 (1H, dd, J 14.3, 6.0, one of ArCH2CH), 3.12 (1H, dd, J 14.3, 8.3, one of ArCH2CH), 3.84 (3H, s, OCH3), 4.42-4.55 (1H, m, CHNO2), 5.11 (2H, OCH2Ph), 6.65 (1H, d, J 1.9, CH), 6.69 (1H, dd, J 8.2, 1.9, CH), 6.80 (1H, d, J8.0, CH), 7.25-7.45 (5H, m, OCH2C6H5).

Provenance & Evidence