反应详情

To a stirred solution of 5-chloro-2-(2,6-diethyl-4-methylphenyl)-3-methoxycyclopent-2-enone (0.530 g, 1.81 mmol) in furan (40 ml) at room temperature is added by syringe pump over two hours a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (0.540 ml, 3.62 mmol) in furan (10 ml). The reaction is stirred at room temperature for a further 30 minutes and then evaporated to dryness under reduced pressure. The residue is diluted with water (50 ml), 2 M aqueous hydrochloric acid (25 ml) is added and the mixture is extracted with ethyl acetate (3×50 ml). The combined organic extracts are washed with brine (20 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated to dryness under reduced pressure. The residue is purified by column chromatography on silica gel to give (1RS,2RS,6SR,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxa-tricyclo[5.2.1.02,6]deca-4,8-dien-3-one.

1. customevaporated to dryness under reduced pressure
2. additionThe residue is diluted with water (50 ml), 2 M aqueous hydrochloric acid (25 ml)
3. additionis added
4. extractionthe mixture is extracted with ethyl acetate (3×50 ml)
5. washThe combined organic extracts are washed with brine (20 ml)
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. customthe filtrate is evaporated to dryness under reduced pressure
9. customThe residue is purified by column chromatography on silica gel