Reaction #3499

Reaction equation

water

sodium hydride

methyl N-methoxycarbamate

chloromethylpropargyl ether

→

methyl N-methoxy-N-propargyloxymethylcarbamate

Yield 75.9%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Temperaturein this order while being cooled with ice
2. 2
   TemperatureThe mixture was heat-refluxed for 1 hour
3. 3
   workup.ADDITIONwas added to the reaction solution
4. 4
   Extractionthe mixture was extracted with ethyl acetate
5. 5
   OtherThe extract was dried
6. 6
   Concentrationconcentrated
7. 7
   Otherpurified by silica gel column chromatography

Procedure

0.37 g of sodium hydride (60% in oil) was suspended in 10 ml of tetrahydrofuran, and 0.8 g of methyl N-methoxycarbamate and 0.96 g of chloromethylpropargyl ether were added thereto in this order while being cooled with ice. The mixture was heat-refluxed for 1 hour. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was dried, concentrated and purified by silica gel column chromatography to obtain 1.0 g of methyl N-methoxy-N-propargyloxymethylcarbamate.

Source