Reaction #57060

Reaction equation

HCl

n-BuI

LDA

cyclobutane carboxylic acid

→

title compound

1-butylcyclobutanecarboxylic acid

Solvents

THF heptane ethylbenzene

THF

Conditions

Workup

1. 1
   workup.ADDITIONAfter addition
2. 2
   Otherthe cold bath was removed
3. 3
   workup.STIRRINGThe mixture was stirred over night
4. 4
   Extractionthe mixture was extracted with ethyl acetate
5. 5
   WashThe combined organic phase was washed with water and brine

Procedure

To a solution of LDA (30 mL, 2.0M, 60 mmol) in THF/heptane/ethylbenzene and anhydrous THF (30 mL) at 0° C. was added cyclobutane carboxylic acid (3.0 g, 30 mmol) dropwise. After addition was complete, the cold bath was removed, the reaction mixture was stirred at room temperature for 2 hr. Neat n-BuI (3.41 mL, 30 mmol) was added dropwise at room temperature. The mixture was stirred over night. To the mixture was added 2N HCl and the mixture was extracted with ethyl acetate. The combined organic phase was washed with water and brine to afford the title compound as a light yellow oil (quantitative), which was used in the next step without purification.

Source