Methyl chloroformate → Methyl 3-cyclopropylprop-2-ynoate
Reaction equation
[CH:1]1([C:4]#[CH:5])[CH2:3][CH2:2]1.Cl[C:7]([O:9][CH3:10])=[O:8]>C(OCC)C>[CH3:10][O:9][C:7](=[O:8])[C:5]#[C:4][CH:1]1[CH2:3][CH2:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of cyclopropyl acetylene (10.0 g, 148 mmol) in 50 mL of ethyl ether at −78° C. under argon was added methyllithiium (1.4 M in ethyl ether, 107 mL, 150 mmol). This solution was stirred at −78° C. for 1 h. Methyl chloroformate (12.0 mL, 154 mmol) was added. The reaction mixture was warmed to room temperature in 2 h and was quenched with water. The organic layer was separated. The aqueous layer was extracted with ethyl ether (50 mL×3). The combined organic layer was dried over sodium sulfate and evaporated to give cyclopropyl-propynoic acid methyl ester as a yellow oil (13.25 g, 72%).