Reaction #927248

Reaction equation

1,1,2-tribromo-2-(7-hydroxyheptyl)cyclopropane

methyllithium

→

1-(7-hydroxyheptyl)-cyclopropene

Yield 90.0%

Solvents

ether

Conditions

Workup

1. 1
   OtherThe reaction was quenched with saturated ammonium chloride
2. 2
   WashThe reaction mixture was washed with water and brine
3. 3
   Dryingdried over magnesium sulfate
4. 4
   Filtrationfiltered

Procedure

A solution of 1.0 g 1,1,2-tribromo-2-(7-hydroxyheptyl)cyclopropane (2.5 mmol) in 25 ml of ether was treated at −78° C. with 7.2 ml of methyllithium (1.4 M, 10 mmol). After 5 minutes, the reaction mixture was warmed to 0° C. and held at this temperature. The reaction was quenched with saturated ammonium chloride. The reaction mixture was washed with water and brine, dried over magnesium sulfate, filtered and stripped to give 240 mg of 1-(7-hydroxyheptyl)-cyclopropene (90% purity).

Source