HCID 22221627, compound → HCID 10286021, compound

Participants

Reaction Conditions

Reaction Steps

Acid 24 (0.030 g, 0.112 mmole) in 5 mL THF was added a solution of Borane-THF complex (2.0 mL, 2.0 mmole) in THF. After stirring at 65° C. for 6 hours, the THF was evaporated and the residue was poured into 2N HCl and extracted with ethyl acetate. The combined organic phases were washed with saturated sodium bicarbonate, water, brine, and dried with magnesium sulfate. The organic phases were concentrated and the residue was separated by HPLC (70:30, H2O/AcCN) to afford 0.011 g (36%) of benzyl alcohol 25 as a white solid: Mp=258-260° C.; 1H NMR (DMSO-d6) δ 9.81 (s, 1 H), 9.45 (s, 1 H), 7.70 (d, 2 H, J=8.9 Hz), 7.00 (s, 1 H), 6.86 (d, 2 H, J=8.7 Hz), 6.76 (s, 2H), 5.27 (m, 1 H), 4.75 (d, 2 H, J=5.6 Hz); MS 255 (M−H)−

Provenance & Evidence