Formaldehyde → 1-(Hydroxymethyl)-4-propylpyrrolidin-2-one

HRID 1924209Notes

Reaction equation

HRID 1924209 reaction equation
[CH2:1]([CH:4]1[CH2:8][NH:7][C:6](=[O:9])[CH2:5]1)[CH2:2][CH3:3].[CH2:10]=[O:11].[K]>C(O)C>[OH:11][CH2:10][N:7]1[CH2:8][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:5][C:6]1=[O:9]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5462222PotassiumHCID 141781004-Propylpyrrolidin-2-one

Product 1

HCID 113326021-(Hydroxymethyl)-4-propylpyrrolidin-2-oneYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-propylpyrrolidin-2-one x1 (30 g, 0.236 mol), aqueous formaldehyde (37%, 3.5 eq, 0.826 mol, 71 ml), and potassium hydroxyde (0.05 eq, 0.012 mol, 0.662 g) in 150 ml of ethanol is refluxed for 24 hours. After evaporation of the solvent under reduced pressure, the crude product is poured in saturated NaHCO3 aqueous solution and then extracted with CH2Cl2. The cumulated organic layers are dried over MgSO4, filtered and evaporated under reduced pressure to yield compound 1-(hydroxymethyl)-4-propylpyrrolidin-2-one x2 as a colorless oil.

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. additionthe crude product is poured in saturated NaHCO3 aqueous solution
  3. extractionextracted with CH2Cl2
  4. dry with materialThe cumulated organic layers are dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fc00ed2eba034fbe9565f03fd86f697d
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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