反应详情

Dissolve 5-methylene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (10.00 g, 48.48 mmol) in CHCl3 (125 mL) and add 4-(dimethylamino)pyridinium tribromide (19.35 g, 53.32 mmol). Stir at room temperature for 2.5 h and quench with saturated aqueous Na2SO3. Separate layers, wash organics with saturated aqueous NaHCO3, then H2O. The dried organics (MgSO4) and concentrated to a yellow oil. Purify crude product by loading onto a 20 g plug of silica gel and eluting with hexanes until eluent shows no UV activity. Combine and concentrate hexane washes to afford 13.01 g (94%) of the title compound as a white solid, mp 73.6° C. HPLC shows 99% purity.

1. customquench with saturated aqueous Na2SO3
2. washSeparate layers, wash organics with saturated aqueous NaHCO3
3. concentrationThe dried organics (MgSO4) and concentrated to a yellow oil
4. customPurify crude product
5. washeluting with hexanes until eluent shows no UV activity
6. concentrationCombine and concentrate hexane washes