反应详情

A mixture of ((1,1′-biphenyl)-4-yl)phenylmethanone (0.01 mol) in THF (200 ml) was stirred at room temperature under N2 flow. Vinylmagnesium chloride (0.011 mol; 1M solution in THF) was added dropwise. The mixture was stirred at room temperature for 1 hour. HCl (150 ml) was added. The mixture was stirred at room temperature for 1 hour and extracted with DIPE. The organic layer was separated, washed once with a saturated K2CO3 solution, twice with H2O and once with a saturated NaCl solution, then dried, filtered and the solvent was evaporated. This fraction was purified by column chromatography over silica gel (eluent: CH2Cl2hexane/EtOAc 50/30/20). Two pure fractions were collected and their solvents were evaporated, yielding 8.8 g (29%) of 4-(3-chloro-1-phenyl-1-propenyl)(1,1′-biphenyl) (interm. 22).

1. stirringThe mixture was stirred at room temperature for 1 hour
2. stirringThe mixture was stirred at room temperature for 1 hour
3. extractionextracted with DIPE
4. customThe organic layer was separated
5. washwashed once with a saturated K2CO3 solution, twice with H2O and once with a saturated NaCl solution
6. customdried
7. filtrationfiltered
8. customthe solvent was evaporated
9. customThis fraction was purified by column chromatography over silica gel (eluent: CH2Cl2hexane/EtOAc 50/30/20)
10. customTwo pure fractions were collected
11. customtheir solvents were evaporated