Reaktion #52344

Reaktionsgleichung

6-methoxy-4,4-dimethyl-1,2,3,4-tetrahydronaphthalene-1-one

→

title compound

Ausbeute 52.0%

6-Hydroxy-4,4-dimethyl-1,2,3,4-tetrahydronaphthalene-1-one

Ausbeute 52.0%

Lösungsmittel

boron tribromide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to −78° C.
2. 2
   Sonstigequenched
3. 3
   workup.ADDITIONdiluted with saturated aqueous sodium bicarbonate solution
4. 4
   Extraktionthe aqueous phase was extracted with dichloromethane (×2)
5. 5
   TrocknenThe combined organic phase was dried over anhydrous sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated in vacuo to an oil

Vorschrift

A stirred, cooled (−78° C.) solution of 6-methoxy-4,4-dimethyl-1,2,3,4-tetrahydronaphthalene-1-one Intermediate 9, 0.8, 3 mmol) under argon was treated with a 1M solution of boron tribromide (10 mL). The reaction mixture was allowed to warm to ambient temperature and stirred overnight. The reaction mixture was cooled to −78° C., quenched and diluted with saturated aqueous sodium bicarbonate solution and the aqueous phase was extracted with dichloromethane (×2). The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to an oil. Flash column chromatography over silica gel (230-400 mesh) using 30% ethyl acetate in hexane as the eluent afforded the title compound (0.3 g, 52%) as a yellow viscous oil.

Quelle