반응 #7949

반응 방정식

BBr3

butyl-4,8-dimethyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

→

butyl-4,8-dimethyl-7-hydroxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

용매

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   온도cooled in an acetone-dry ice bath
2. 2
   기타The cooling bath was removed
3. 3
   workup.ADDITIONThe reaction mixture was diluted with EtOAc (20 mL)
4. 4
   세척washed with water (20 ml)
5. 5
   workup.ADDITIONcontaining 2N HCl (2 mL)
6. 6
   건조dried over MgSO4
7. 7
   여과filtered
8. 8
   기타evaporated under vacuum
9. 9
   기타The crude product was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate
10. 10
    세척The UV visible product band was eluted with EtOAc
11. 11
    기타the solvent evaporated under vacuum

실험 절차

A solution of 9a butyl-4,8-dimethyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (84 mg, 0.28 mmol) in anhydrous CH2Cl2 (3 mL) was placed under a nitrogen atmosphere, cooled in an acetone-dry ice bath, and treated with 1M BBr3 in CH2Cl2 (1.11 mL, 1.11 mmol). The cooling bath was removed and the reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was diluted with EtOAc (20 mL), washed with water (20 ml) containing 2N HCl (2 mL) followed by brine (10 mL), dried over MgSO4, filtered, and evaporated under vacuum. The crude product was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate, developing with 10% EtOAc in CH2Cl2. The UV visible product band was eluted with EtOAc and the solvent evaporated under vacuum. The residue was lyophilized from benzene-methanol to afford 9a butyl-4,8-dimethyl-7-hydroxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one as a solid.

출처