1-(2-Hydroxyethyl)-2-pyrrolidinone → (2-Oxopyrrolidin-1-yl)acetaldehyde

HRID 2364426Notes

Reaction equation

HRID 2364426 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

HCID 769801-(2-Hydroxyethyl)-2-pyrrolidinoneHCID 159087Triacetoxyperiodinane

Product 1

HCID 22405515(2-Oxopyrrolidin-1-yl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue was triturated with Et2O
  3. filtrationAfter filtration of the solids
  4. customthe mother liquor was evaporated in vacuo
  5. 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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