反应详情

温度

0 °C

To a suspension of 5-(Phenylethynyl)nicotinaldehyde (7.0 g, 33.8 mmol) in ethanol (150 mL), immersed in a room temperature bath to moderate any potential exotherm, was added sodium borohydride (0.639 g, 16.9 mmol) in one portion. After 30 min at room temperature, the reaction was cooled to 0° C. and quenched by the cautious addition of saturated ammonium chloride. The reaction was concentrated and partitioned between water and ether. The aqueous was extracted with ether (2×). The organics were washed with brine, dried over magnesium sulfate, and concentrated to give a faint yellow solid. Material was used without purification. 1H NMR (CDCl3) δ: 8.39-8.81 (m, 2H), 7.88 (s, 1H), 7.51-7.61 (m, 2H), 7.34-7.44 (m, 3H), 4.77 (s, 2H), 3.21 (br. s., 1H). 13C NMR (CDCl3) δ: 151.1, 147.1, 137.3, 131.8, 129.0, 128.6, 122.5, 93.0, 85.9, 62.3. Mass spec.: 210.1 (MH)+.

1. customimmersed in a room temperature
2. customquenched by the cautious addition of saturated ammonium chloride
3. concentrationThe reaction was concentrated
4. custompartitioned between water and ether
5. extractionThe aqueous was extracted with ether (2×)
6. washThe organics were washed with brine
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated
9. customto give a faint yellow solid
10. customMaterial was used without purification