Methanol → HCID 25133549, compound

Participants

Reaction Conditions

Reaction Steps

Compound 5 (0.8 g, 1.8 mmol) was dissolved in dry Et2O (8.5 mL) and the solution was cooled to 0° C., afterward lithium borohydride (0.12 g, 5.4 mmol) and dry methanol (0.22 mL, 5.4 mmol) were sequentially added. The resulting suspension was stirred at 23° C. for 24 h, then a few drops of 6 N HCl were added and the salts were filtered off. The filtrate was concentrated under reduced pressure and the residue was purified by flash-chromatography (1:1 EtOAc/Hex) to furnish 0.61 g (93%) of 6a as a colourless oil: [α]D20=−15.6 (c 3.1, CHCl3); 1H NMR (CDCl3) δ 7.70-7.65 (m, 4H), 7.44-7.32 (m, 6H), 3.82-3.77 (m, 1H), 3.53-3.48 (m, 2H), 3.45-3.41 (m, 2H), 1.65-1.47 (m, 4H), 1.05 (s, 9H); 13C NMR (CDCl3) δ 135.9, 135.7, 133.8, 133.7, 130.1, 129.8, 127.7, 127.6, 73.6, 65.7, 62.7, 29.7, 28.0, 27.0, 19.3.

Provenance & Evidence