Reaction #1494

Reaction equation

ethyl 2-bromoacetate

3,4-dihydro-4,4-dimethyl-7-bromo-naphthalen-1(2H)-one

7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one

Compound G

7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one

→

title compound

(±)Ethyl 2-(1-hydroxy-1,2,3,4-tetrahydro-4,4-dimethyl-7-bromo-naphthalen-1-yl)acetate

Solvents

benzene

benzene

Conditions

Workup

1. 1
   TemperatureThe resulting mixture was heated for 2 h
2. 2
   Otherthe solution decanted from the residual solids
3. 3
   WashThe solids were washed with EtOAc
4. 4
   Washthe combined organic layers were washed with cold 15% H2SO4, saturated aqueous NaHCO3, and saturated aqueous NaCl
5. 5
   Dryingbefore being dried over MgSO4
6. 6
   OtherRemoval of the solvents undr reduced pressure and column chromatography (10% EtOAc-hexanes)

Procedure

To a suspension of Zn (1.20 g, 18.4 mmol) in 10 mL benzene at 100° C. was slowly added a solution of ethyl 2-bromoacetate (658.0 mg, 3.94 mmol) and 3,4-dihydro-4,4-dimethyl-7-bromo-naphthalen-1(2H)-one (Compound G, 500.0 mg, 1.97 mmol) in 20.0 mL benzene. The resulting mixture was heated for 2 h, cooled to room temperature, and the solution decanted from the residual solids. The solids were washed with EtOAc and the combined organic layers were washed with cold 15% H2SO4, saturated aqueous NaHCO3, and saturated aqueous NaCl before being dried over MgSO4. Removal of the solvents undr reduced pressure and column chromatography (10% EtOAc-hexanes) afforded the title compound as a yellow oil.

Source