Water → methyl N-methoxy-N-propargyloxymethylcarbamate

HRID 3403Notes

Reaction equation

HRID 3403 reaction equation
[H-].[Na+].[CH3:3][O:4][NH:5][C:6](=[O:9])[O:7][CH3:8].Cl[CH2:11][O:12][CH2:13][C:14]#[CH:15].O>O1CCCC1>[CH3:3][O:4][N:5]([CH2:11][O:12][CH2:13][C:14]#[CH:15])[C:6](=[O:9])[O:7][CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 122413411-Propyne, 3-(chloromethoxy)-HCID 12663380methyl N-methoxycarbamate

Product 1

HCID 18935025methyl N-methoxy-N-propargyloxymethylcarbamateYield 75.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. temperaturein this order while being cooled with ice
  2. temperatureThe mixture was heat-refluxed for 1 hour
  3. additionwas added to the reaction solution
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe extract was dried
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-b317ab1e31f1484d8c7fa6fc2ad9a7be
Source dataset
uspto-grants-1998_03
Patent number
US05733935

Reaction notes

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