Reaction #969895

Reaction equation

hydrochloric acid

N-methylmorpholine

1-(4-methoxyphenyl)cyclopropane carboxylic acid

lithium aluminum hydride

→

1-(4-methoxyphenyl)cyclopropane carboaldehyde

Yield 84.0%

Solvents

water

tetrahydrofuran

Conditions

Workup

1. 1
   workup.STIRRINGstirred at room temperature for 30 min
2. 2
   Extractionextracted with ethyl acetate
3. 3
   DryingThe organic layer was dried over anhydrous sodium sulfate
4. 4
   Concentrationconcentrated in vacuo
5. 5
   workup.DISSOLUTIONThe obtained residue was dissolved in dichloromethane (15 mL)
6. 6
   workup.STIRRINGstirred at room temperature for 1.5 hours
7. 7
   FiltrationThe reaction solution was filtered
8. 8
   Concentrationconcentrated in vacuo
9. 9
   OtherThe obtained residue was purified

Procedure

Under an argon atmosphere, a solution of 1-(4-methoxyphenyl)cyclopropane carboxylic acid (2.00 g, 10.4 mmol) in tetrahydrofuran (20 mL) was added with lithium aluminum hydride (513 mg, 13.5 mmol) at 0° C., and the resultant was stirred at room temperature for 2 hours. The resultant was added sequentially with water and hydrochloric acid at 0° C., stirred at room temperature for 30 min and then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was dissolved in dichloromethane (15 mL). The resultant was sequentially added with molecular sieves 4β (1.80 g), N-methylmorpholine (1.83 g, 15.6 mmol) and tetrapropylammonium perruthenate (1.83 mg, 0.520 mmol) at 0° C., and stirred at room temperature for 1.5 hours. The reaction solution was filtered using celite, and concentrated in vacuo. The obtained residue was purified using column chromatography (hexane:ethyl acetate=4:1), and 1-(4-methoxyphenyl)cyclopropane carboaldehyde (1.54 g, 84.0%) was obtained.

Source