Lithium borohydride → HCID 10715906, compound

Participants

Reaction Steps

A solution of 6 (400 mg, 1.0 mmol) in anhydrous THF (12 mL) under argon was cooled to −20 to −25° C. and LiBH4 (55 mg, 2.5 mmol) was added in portions. The reaction was monitored by TLC (silica, hexanes/ethyl acetate (4:1)), and when no starting material was detected (20-25 min), the reaction was quenched with cold water (30 mL). The aqueous layer was extracted with CH2Cl2 and the organic layer was dried (Na2SO4), concentrated, and purified by flash column chromatography [silica, hexanes/ethyl acetate containing 1% Et3N (3:1)] yielding a gum (330 mg, 82%). 1H NMR δ 1.62 (s, 9H), 3.61 (br, 1H), 4.66 (d, J=7.2 Hz, 2H), 6.25 (d, J=3.6 Hz, 1H), 7.18 (d, J=8.1 Hz, 2H), 7.22 (d, J=3.6 Hz, 1H), 7.71 (d, J=8.1 Hz, 2H); 13C NMR δ 27.8, 55.3, 84.7, 92.4, 111.2, 121.3, 127.9, 130.0, 130.4, 134.1, 137.5, 149.8; FAB-MS obsd 399.0336, calcd 399.0331 (C16H18INO3).

Provenance & Evidence