Diketene → N-(2,3-Dihydroxypropyl)-3-oxobutanamide
Reaction equation
C[NH:2][CH2:3][CH:4]([OH:7])[CH2:5][OH:6].[CH2:8]=[C:9]1[O:13][C:11](=[O:12])[CH2:10]1>O1CCCC1>[OH:7][CH:4]([CH2:5][OH:6])[CH2:3][NH:2][C:11](=[O:12])[CH2:10][C:9](=[O:13])[CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 22.5 g (0.21 mol) 3-methylamino-1,2-propanediol in 200 ml of tetrahydrofuran was added dropwise to a solution of 18 g of diketene (0.21 mol) in 200 ml of 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 32.00 g (0.17 mol, 79% yield) of a colorless oil.
Workup
- customThe reaction mixture was evaporated
- customthe residue purified by column chromatography
Sources & evidence
- ORD record
- ord-06336af4522942549e3e765d5034a6a3
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394324B2
Reaction notes
Loading…