Carbon Dioxide → HCID 19261789, compound

Participants

Reaction Conditions

Reaction Steps

Magnesium turnings (0.45 g, 18.5 mmol) under tetrahydrofuran (5 mL) was activated with grain of iodine and with 1,2-dibromoethane (0.25 mL) and after the reaction was over, a solution of vinyl bromide (2.0 g, 18.5 mmol) in tetrahydrofuran (30 mL) was added (dry ice condenser, nitrogen atmosphere). The reaction start immediately and the remaining part of the vinyl bromide solution was added dropwise under stirring at such a rate as to maintain the mixture under reflux (30 min). The mixture was stirred at 65° C. for next 30 min, cooled to 35° C. and then over 30 min a solution of the above ketone (1.75 g, 6.15 mmol) in tetrahydrofuran (35 mL) was added dropwise. The mixture was stirred at 35° C. for 3 h and then poured on a mixture of crushed ice (100 g) and 25% solution of ammonium chloride (30 mL). The mixture was extracted with diethyl ether (50 mL, 2×20 mL), combined organic solutions were washed with brine, dried (MgSO4) and evaporated in vacuo. The residue (2.5 g) was purified by flash-chromatography on silica gel (Fluka 60, 80 g, hexane/benzene 6:4) to yield 1.65 g (86%) of 2-phenyl-5-vinyl-10,11 dihydro-5H-dibenzo[a,d]cyclohepten-5-ol.

Provenance & Evidence