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温度

0 °C

2-(1-Hexyn-1-yl)-N-methyl-N,4-bis(methyloxy)benzamide (79) (0.42 g, 1.51 mmol) was dissolved in THF (10 mL). Cooled to 0° C. in an ice bath, benzylmagnesium chloride (2 M in THF, 1.50 mL, 3.0 mmol) was added. The mixture was stirred at 0° C. for 3 h, quenched with saturated aqueous NH4Cl and extracted with EtOAc (2×50 mL). The combined organic extract was washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a yellow oil. The crude product was purified by flash chromatography over SiO2 eluted with a gradient from hexanes to 15% EtOAc in hexanes to give 0.37 g (80%) of the title compound (80) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 0.93 (t, J=7.3 Hz, 3H), 1.40-1.55 (m, 2H), 1.55-1.65 (m, 2H), 2.46 (t, J=7.2 Hz, 2H), 3.83 (s, 3H), 4.44 (s, 2H), 6.82 (dd, J1=8.8 Hz, J2=2.7 Hz, 1H), 6.96 (d, J=2.5 Hz, 1H), 7.20-7.34 (m, 5H), 7.65 (d, J=8.7 Hz, 1H). LCMS (ESI): m/z 307 (M+H)+.

1. customquenched with saturated aqueous NH4Cl
2. extractionextracted with EtOAc (2×50 mL)
3. extractionThe combined organic extract
4. washwas washed with brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationthe filtrate was concentrated
8. customto give the crude product as a yellow oil
9. customThe crude product was purified by flash chromatography over SiO2
10. washeluted with a gradient from hexanes to 15% EtOAc in hexanes