2-Methoxyethylamine → N-(2-Methoxyethyl)-3-oxobutanamide

HRID 1055210Notes

Reaction equation

HRID 1055210 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[CH2:6]=[C:7]1[O:11][C:9](=[O:10])[CH2:8]1>O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:9](=[O:10])[CH2:8][C:7](=[O:11])[CH3:6]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 12661Diketene

Product 1

HCID 337172N-(2-Methoxyethyl)-3-oxobutanamideYield 83.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

33 ml (0.38 mol) methoxyethylamine were added dropwise to a solution of 30 g of diketene (0.36 mol) in 300 ml tetrahydrofuran at −5 to 0° C. After 1 h stirring at 0° C. no more starting material was detected by thin layer chromatography. The reaction mixture was evaporated and the residue purified by column chromatography. This gave 47.15 g (0.30 mol, 83% yield) of a white solid.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-ecd36131f5e24b2faf1a9b1fa34723e9
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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