反应详情

A solution of cyclohex-1-enecarboxylic acid methyl ester 1 (5.15 g; 36.7 mmol), tetrabutyl ammonium fluoride (55.10 mL; 1 M in THF; 55.1 mmol) and nitromethane (3.97 mL; 73.5 mmol) in tetrahydrofuran (60 mL) was heated to reflux for 4 hours. After cooling to room temperature, the reaction mixture was diluted with diethyl ether (500 mL), washed with 2N HCl (2×100 mL) and then with brine (2×100 mL). The phases were separated. The organic phase was dried over MgSO4 and concentrated in vacuo. The crude mixture was purified over silica gel chromatography (EtOAc/heptane 1:4) to give 2 (5.46 g; cis and trans isomers; 73%) as a pale yellow liquid.

1. temperatureto reflux for 4 hours
2. washwashed with 2N HCl (2×100 mL)
3. customThe phases were separated
4. dry with materialThe organic phase was dried over MgSO4
5. concentrationconcentrated in vacuo
6. customThe crude mixture was purified over silica gel chromatography (EtOAc/heptane 1:4)
7. customto give 2 (5.46 g; cis and trans isomers; 73%) as a pale yellow liquid