Reaction #684959

Reaction equation

water

potassium carbonate

t-butyl bromide

4-pentynoic acid

→

title compound

t-Butyl 4-pentynoate

Solvents

N,N-dimethylacetamide

Conditions

Workup

1. 1
   Extractionthe reaction mixture was extracted with ethyl acetate
2. 2
   Washwashed with water
3. 3
   Dryingdried over anhydrous magnesium chloride
4. 4
   Filtrationfiltered through silica gel
5. 5
   ConcentrationThe filtrate was concentrated under reduced pressure

Procedure

Benzyltriethylammonium chloride (5.92 g), potassium carbonate (93.4 g), and t-butyl bromide (143 ml) were added to a solution of 4-pentynoic acid (2550 mg) in N,N-dimethylacetamide (230 ml), and this reaction mixture was stirred at 55° C. for 24 hours. After water was added, the reaction mixture was extracted with ethyl acetate, washed with water, dried over anhydrous magnesium chloride, and then filtered through silica gel. The filtrate was concentrated under reduced pressure to give the title compound (2.10 g). This compound was used in the following reaction without further purification.

Source