反应详情

To a solution of 3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (2 g, 8.7 mmol) in dry tetrahydrofuran (25 ml) at −78° C. is added a solution of lithium diisopropylamide (5.8 ml, 10.4 mmol, 1.8 M in hexane/THF/ethylbenzene) dropwise over 20 minutes. The resultant solution is stirred for 30 minutes at −78° C. before adding 4-methoxy-cyclohexanecarbaldehyde (1.4 g, 9.8 mmol) dissolved in tetrahydrofuran (15 ml). The reaction mixture is allowed to warm to room temperature overnight then diluted with water, acidified with 2 N HCl and extracted with ethyl acetate (3×15 ml). The combined organic extract are dried over magnesium sulfate, filtered and evaporated under reduced pressure to give an brown oil. The residue is purified by flash chromatography to 5-[Hydroxy-(4-methoxy-cyclohexyl)-methyl]-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (1.7 g).

1. extractionextracted with ethyl acetate (3×15 ml)
2. extractionThe combined organic extract
3. dry with materialare dried over magnesium sulfate
4. filtrationfiltered
5. customevaporated under reduced pressure
6. customto give an brown oil
7. customThe residue is purified by flash chromatography to 5-[Hydroxy-(4-methoxy-cyclohexyl)-methyl]-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (1.7 g)