Acetic Acid → 4-Hydroxy-3-(3-hydroxy-3-phenylpropyl)-2H-1-benzopyran-2-one

Participants

Reaction Steps

A rapidly stirred suspension of the product obtained in Example 16 (0.21 g, 0.71 mmol) in 10 mL of methanol was treated portionwise with 0.08 g (2.1 mmol) of sodium borohydride. The reaction mixture was stirred at room temperature for 36 hours. Glacial 30 acetic acid (3 mL) was added, and the mixture was concentrated. The residue was partitioned between ethyl acetate and water, and the organic layer was dried and concentrated. The product was chromatographed on silica gel, eluting with 4:1 chloroform: ethyl acetate, to give the title compound, m.p. 138°-140° C. NMR (CDCl3) δ1.25 (m, 2H), 2.88 (m, 2H), 4.66 (dd, 1H), 7.32 (m, 7H), 7.52 (t, 1H), 7.90 (d, 1H).

Provenance & Evidence