Reaction #927268

Reaction equation

5-Hexyn-1-ol

Water

2-octylcycloprop-2-ene-1-carbonyl chloride

triethylamine

→

hex-5-yne 2-octylcycloprop-2-ene-1-carboxylate

Yield 9.6%

Solvents

ether

ether

Conditions

Workup

1. 1
   Otherthe resulting mixture was transferred to a separatory funnel
2. 2
   Otherthe phases were separated
3. 3
   WashThe organic layer was washed with water and brine
4. 4
   Dryingdried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   OtherThe product was chromatographed on silica gel

Procedure

To a solution of 2-octylcycloprop-2-ene-1-carbonyl chloride (330 mg, 1.5 mmol) in 5 ml of ether is added 1.5 ml of triethylamine. 5-Hexyn-1-ol (0.18 g, 1.8 mmol) was added to the reaction mixture, which was stirred at room temperature over the weekend. Water and additional ether were added, and the resulting mixture was transferred to a separatory funnel and the phases were separated. The organic layer was washed with water and brine, dried over MgSO4, filtered and stripped. The product was chromatographed on silica gel to give 40 mg of 60% pure hex-5-yne 2-octylcycloprop-2-ene-1-carboxylate containing roughly 40% 2-octylcycloprop-2-ene-1-carboxylic acid.

Source