反应详情

A solution of n-butyllithium in hexanes (32.2 ml, 2.5 M) was added dropwise under a nitrogen atmosphere to ethylene glycol (60 ml) at 10° C. When addition was complete the mixture was stirred for 0.5 h at room temperature. A solution of 3-bromo-1-(3-methoxyphenyl)-1-(2-methylphenyl)-1-propene (24.4 g, 77 mmol) in toluene (50 ml) was added and the reaction mixture was stirred at room temperature for 4 days and at 65° C. for 6 h. The solvent was evaporated in vacuo, water (250 ml) was added and the mixture was extracted with ethyl acetate (2×200+100 ml). The combined organic phases was dried over magnesium sulphate and the solvent was evaporated in vacuo. Flash chromatography of the residue on silica gel (320 g) using a mixture of cyclohexane and ethyl acetate gradient as eluent provided 16.6 g (72%) of 2-(3-(3-methoxyphenyl)-3-(2-methylphenyl)-2-propen-1-yloxy)ethanol.

1. additionWhen addition
2. stirringthe reaction mixture was stirred at room temperature for 4 days and at 65° C. for 6 h
3. customThe solvent was evaporated in vacuo, water (250 ml)
4. additionwas added
5. extractionthe mixture was extracted with ethyl acetate (2×200+100 ml)
6. dry with materialThe combined organic phases was dried over magnesium sulphate
7. customthe solvent was evaporated in vacuo
8. additiona mixture of cyclohexane and ethyl acetate gradient as eluent