Sodium borohydride → 2-(1-Hydroxyethyl)naphtho(2,3-b)furan-4,9-dione

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[C:1]([C:4]1[O:8][C:7]2[C:9](=[O:18])[C:10]3[C:15]([C:16](=[O:17])[C:6]=2[CH:5]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)(=[O:3])[CH3:2].[BH4-].[Na+]>CN(C=O)C.O>[OH:3][CH:1]([C:4]1[O:8][C:7]2[C:9](=[O:18])[C:10]3[C:15]([C:16](=[O:17])[C:6]=2[CH:5]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH3:2]

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In a 250 ml beaker, 2 grams (8.3 mmoles) of 2-acetyl-naphtho[2,3-b]furan-4,9-dione (prepared in example 2 or 3) was dissolved in 40 ml of DMF with heating. To the solution with stirring, 1 gram (26.4 mmoles) of sodium borohydride in 10 ml of water was added. The mixture was stirred in open air for 30 minutes, then diluted by adding 250 ml of water. The resulting mixture was extracted with 100 ml of dichloromethane twice. The combined organic phase was washed with 200 ml of water, dried with anhydrous sodium sulfate, and evaporated to dryness. The residue was crystallized in ethyl acetate to yield 1.6 gram (6.6 mmoles) of pure product with overall yield 80%. Pure product was characterized by 1H NMR and mass spectrum. 1H NMR (in DMSO) δ 1.47 (d, J=7, 3H), 4.88 (m, 1H), 5.83 (d, J=5, 1H), 6.91 (s, 1H), 7.84-7.90 (m, 2H), 8.06-8.11 (m, 2H). Mass (M+H) is 243.