反应详情

Cyclohexylamine (3.43 ml, 30.0 mmol) was added to pyran-3-one (3000 mg, 30.0 mmol) in benzene (20 mL). The reaction mixture was stirred at RT for 30 min and then refluxed for 2 hr with a dean-stark trap. The benzene was then distilled off and the residue was redissolved in THF (2 mL) and added to BuLi (13.18 ml, 33.0 mmol) in THF (Volume: 30.000 ml) at 0° C. The reaction mixture was stirred at 0° C. for 1 h before 5-bromo-1-pentene (5582 mg, 37.5 mmol) was added. The reaction mixture was stirred at 0° C. for 2 hr. The mixture was cooled and quenched with water. The reaction mixture was extracted with diethyl ether (3×20 mL). The combined organic fractions were washed with water and brine (saturated, 100 mL), dried, filtered and the solvent was evaporated under reduced pressure (400 mmhg). The residue was purified by column chromatography on silica gel to provide the title compound. 1H NMR (500 MHz, CDCl3) δ 5.74-5.86 (m, 1H), 4.92-5.06 (m, 2H), 3.90-4.06 (m, 3H), 3.77-3.85 (m, 1H), 2.41-2.49 (m, 1H), 2.16-2.24 (m, 1H), 2.01-2.12 (m, 2H), 1.72-1.97 (m, 2H), 1.31-1.49 (m, 3H).

1. temperaturerefluxed for 2 hr with a dean-stark trap
2. distillationThe benzene was then distilled off
3. dissolutionthe residue was redissolved in THF (2 mL)
4. additionwas added
5. stirringThe reaction mixture was stirred at 0° C. for 2 hr
6. temperatureThe mixture was cooled
7. customquenched with water
8. extractionThe reaction mixture was extracted with diethyl ether (3×20 mL)
9. washThe combined organic fractions were washed with water and brine (saturated, 100 mL)
10. customdried
11. filtrationfiltered
12. customthe solvent was evaporated under reduced pressure (400 mmhg)
13. customThe residue was purified by column chromatography on silica gel