Reaktion #7945

Reaktionsgleichung

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

BBr3

→

solid

Ausbeute 99.1%

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

Ausbeute 99.1%

Lösungsmittel

CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise by syringe
2. 2
   SonstigeThe cooling bath was removed
3. 3
   workup.ADDITIONThe mixture was diluted with EtOAc (8 mL), water (3 mL) and 1N HCL (1 mL)
4. 4
   workup.STIRRINGshaken vigorously
5. 5
   SonstigeThe EtOAc layer was separated
6. 6
   Waschenwashed with water (3 mL), 1M pH 3 phosphate (3 mL) and brine (3 mL)
7. 7
   Trocknendried over MgSO4
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated under vacuum

Vorschrift

A solution of 9a-butyl-7-methoxy-8-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (28.4 mg, 0.1 mmol) in anhydrous CH2Cl2 (1.7 mL) was stirred under a nitrogen atmosphere and cooled in a dry ice-acetone bath while 1M BBr3 in CH2Cl2 (0.30 mL, 0.3 mmol) was added dropwise by syringe. The cooling bath was removed and the reaction mixture was stirred at room temperature for 4 hours. The mixture was diluted with EtOAc (8 mL), water (3 mL) and 1N HCL (1 mL) and shaken vigorously. The EtOAc layer was separated, washed with water (3 mL), 1M pH 3 phosphate (3 mL) and brine (3 mL), dried over MgSO4, filtered and evaporated under vacuum to give an ochre solid (26.8 mg). The crude product was suspended in CDCl3 (1 mL) and filtered. The solid portion was dried under vacuum to afford 9a-butyl-7-hydroxy-8-methyl-1,2,9,9a-3H-tetrahydro-fluoren-3-one as an olive colored powder.

Quelle