반응 #2146738
ord-0c5908a536a04260b79d931a326de94d
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후처리
- 1온도cooled to −78° C.
- 2온도cooled to −78° C.
- 3workup.STIRRINGAfter 1 h stirring
- 4온도the reaction mixture warmed to 20° C
- 5추출The aq. phase was extracted with diethyl ether
- 6건조phases dried (MgSO4)
- 7농축concentrated
- 8workup.ADDITIONA solution of the residue (4.9 g) in toluene (4.9 ml) was treated with para-toluene sulfonic acid monohydrate (20 mg)
- 9온도refluxed overnight
- 10온도The reaction mixture was cooled
- 11workup.ADDITIONtreated with a saturated aqueous solution of NaHCO3
- 12추출the aqueous phase was extracted with diethyl ether
- 13건조The combined organic phases were dried (MgSO4)
- 14농축concentrated
실험 절차
At −78° C., a solution of diisopropylamine (6.6 g, 34 mmol) in tetrahydrofuran (23 ml) was treated with n-butyl lithium (21 ml, 1.6M in hexane, 34 mmol). The resulting solution was warmed to 0° C., cooled to −78° C., and treated with a solution of 1-(rel-(1R,2S,6S)-6-ethyl-2-methylcyclohex-3-enyl)ethan-1-one (4.5 g, 27 mmol) in tetrahydrofuran (23 ml). The resulting solution was stirred 20 min. at −20° C., cooled to −78° C. and treated with a solution of acetaldehyde (1.8 g, 41 mmol) in tetrahydrofuran (23 ml). After 1 h stirring, aqueous 1N HCl (50 ml) was added and the reaction mixture warmed to 20° C. The aq. phase was extracted with diethyl ether and the combined org. phases dried (MgSO4), and concentrated. A solution of the residue (4.9 g) in toluene (4.9 ml) was treated with para-toluene sulfonic acid monohydrate (20 mg) and refluxed overnight. The reaction mixture was cooled, treated with a saturated aqueous solution of NaHCO3 and the aqueous phase was extracted with diethyl ether. The combined organic phases were dried (MgSO4) and concentrated. FC (550 g SiO2, hexane/diethyl ether 9:1) of the crude product gave (2E)-1-(rel-(1R,2S,6S)-6-ethyl-2-methylcyclohex-3-enyl)but-2-en-1-one (2.9 g, 56%).