Reaction #504236

Reaction equation

3,5-dimethoxybenzonitrile

cyclopentylmagnesium chloride

water

sulfuric acid

→

title compound

Yield 82.0%

Cyclopentyl-(3,5-dimethoxy-phenyl)-methanone

Yield 82.0%

Solvents

diethyl ether

THF

Conditions

Workup

1. 1
   OtherThe resulting reaction mixture
2. 2
   Temperaturewas refluxed for 1 h
3. 3
   Washwashed with water and brine
4. 4
   ExtractionThe organic extract
5. 5
   Dryingwas dried over anhydrous sodium sulfate
6. 6
   Concentrationconcentrated
7. 7
   Otherpurified on a silica gel column

Procedure

To a solution of 3,5-dimethoxybenzonitrile (5.0 g) in anhydrous THF (60 mL) were added a solution of cyclopentylmagnesium chloride (20 mL of 2 M solution in diethyl ether) and cuprous bromide (88 mg). The resulting reaction mixture was refluxed for 1 h. Then water (10 mL) and 10% sulfuric acid (20 mL) were added and the resulting mixture was stirred at room temperature overnight. Then the reaction mixture was diluted with diethyl ether and washed with water and brine. The organic extract was dried over anhydrous sodium sulfate, concentrated and purified on a silica gel column using ethyl acetate and hexanes to yield 5.9 of the title compound (82% yield). HRMS calcd for C14H18O3 [M+H]+ 253.1329, observed 253.1328.

Source