反应详情

A suspension of (4-cyanonaphthalen-1-yl)acetic acid (100 mg, 0.47 mmol) in THF (6 mL) was treated with borane dimethyl sulfide complex (2M, 0.47 mL, 0.94 mmol) and the reaction was stirred for 3 hours at room temperature. The reaction was quenched with methanol and the mixture was partitioned with ethyl acetate and 2N HCl/water. The aqueous was extracted again with ethyl acetate and the organic layers were washed with brine, dried over sodium sulfate and evaporated. The residue was purified on a CombiFlash Rf (12 gm, gradient 10-80% ethyl acetate in hexanes) to afford the title alcohol as an oil. 1H-NMR (500 MHz, CDCl3) δ ppm 1.80 (br s, 1H), 3.48 (t, J=6.4 Hz, 2H), 4.10 (t, J=6.4 Hz, 2H), 7.52 (d, J=7.3 Hz, 1H), 7.75 (m, 2H), 7.92 (d, J=7.2 Hz, 1H), 8.22 (d, J=8.2 Hz, 1H). 8.34 (d, J=8.0 Hz, 1H).

1. additionwas treated with borane dimethyl sulfide complex (2M, 0.47 mL, 0.94 mmol)
2. customThe reaction was quenched with methanol
3. customthe mixture was partitioned with ethyl acetate and 2N HCl/water
4. extractionThe aqueous was extracted again with ethyl acetate
5. washthe organic layers were washed with brine
6. dry with materialdried over sodium sulfate
7. customevaporated
8. customThe residue was purified on a CombiFlash Rf (12 gm, gradient 10-80% ethyl acetate in hexanes)