反应详情

温度

45 °C

N-(3-(3-(3-ethyl-3-hydroxypentyl)phenyl)propyl)-2,2,2-trifluoroacetamide (12) (0.660 g, 1.93 mmol) was dissolved in MeOH (15 mL), and an aqueous solution of K2CO3 (0.42 g/3 mL) was added. The resulting mixture was stirred at 45° C. for 4 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure then partitioned between EtOAc (50 mL) and water (50 mL). The combined organics were dried over Na2SO4, and concentrated under reduced pressure. Purification by flash chromatography (80 to 100% (9:1 EtOAc: 7M NH3 in MeOH):hexanes gradient) gave 1-(3-(3-aminopropyl)phenyl)-3-ethylpent-1-yn-3-ol (13) as a light yellow oil. Yield (0.421 g, 89%): 1H NMR (400 MHz, DMSO-d6) δ 7.15-7.26 (m, 4H), 5.11 (s, 1H), 2.56 (t, J=7.6 Hz, 2H), 2.47 (t, J=5.2 Hz, 2H), 1.55-1.65 (m, 6H), 1.39 (br s, 2H), 0.97 (t, J=7.6 Hz, 6H).

1. temperatureAfter cooling to room temperature
2. concentrationthe reaction mixture was concentrated under reduced pressure
3. customthen partitioned between EtOAc (50 mL) and water (50 mL)
4. dry with materialThe combined organics were dried over Na2SO4
5. concentrationconcentrated under reduced pressure
6. customPurification by flash chromatography (80 to 100% (9:1 EtOAc: 7M NH3 in MeOH):hexanes gradient)