Reaction #927271

Reaction equation

HCl

Methyl chloroformate

7-cycloprop-1-enyl-heptanoic acid

diethylamine

→

colorless liquid

7-Cycloprop-1-enyl-heptanoic Acid Diethylamide

Solvents

triethyl amine

ether

water

ether

Conditions

Workup

1. 1
   Temperaturewas still cooled in an ice bath
2. 2
   workup.STIRRINGthe reaction was stirred for one half hour
3. 3
   OtherThe phases were separated
4. 4
   Washthe organic phase was washed with water, 1N sodium hydroxide, water and brine
5. 5
   DryingThe organic phase was dried over magnesium sulfate
6. 6
   Filtrationfiltered

Procedure

A solution of 7-cycloprop-1-enyl-heptanoic acid (0.25 g, 1.5 mmol) in 10 ml of ether was cooled in an ice bath and treated with 0.3 mL of triethyl amine. Methyl chloroformate (0.16 g, 17 mmol) was added, and the reaction was stirred for 1.5 hours. Excess diethylamine was added while the reaction was still cooled in an ice bath, and the reaction was stirred for one half hour. Additional ether and water were added, and the aqueous phase was acidified to pH 1 with aqueous HCl. The phases were separated, and the organic phase was washed with water, 1N sodium hydroxide, water and brine. The organic phase was dried over magnesium sulfate, filtered and stripped. Column chromatography gave 70 mg of colorless liquid 7-cycloprop-1-enyl-heptanoic acid diethylamide (Compound 48) in 74% purity.

Source