1-(2-Hydroxyethyl)-2-pyrrolidinone → (2-Oxopyrrolidin-1-yl)acetaldehyde
Reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[O:9].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C(Cl)Cl>[O:9]=[C:5]1[CH2:6][CH2:7][CH2:8][N:4]1[CH2:3][CH:2]=[O:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of N-(2-Hydroxyethyl)-2-pyrrolidone (5.00 g, 38.8 mmol) and triacetoxyperiodinane (24.6 g, 58.0 mmol) in CH2Cl2 was stirred at ambient temperature for approximately 64 hours. The reaction mixture was evaporated in vacuo and the residue was triturated with Et2O. After filtration of the solids, the mother liquor was evaporated in vacuo to provide the product as a crude oil: 1H NMR (CDCl3) δ 9.60 (1H, s), 4.16 (2H, s), 3.46 (2H, t, J=7 Hz), 2.45 (2H, t, J=8 Hz), 2.11 (2H, m).
Workup
- customThe reaction mixture was evaporated in vacuo
- customthe residue was triturated with Et2O
- filtrationAfter filtration of the solids
- customthe mother liquor was evaporated in vacuo
- customto provide the product as a crude oil
Sources & evidence
- ORD record
- ord-3d0b21a93cc644229f20f714695222a5
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691991B2
Reaction notes
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