Acetone → HCID 9855817, compound

HRID 1018064Notes

Reaction equation

HRID 1018064 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.C[C:19](C)=[O:20].C[O-:23].[Na+]>CO>[CH2:1]([N:8]1[CH2:12][CH:11]([O:20][CH3:19])[CH:10]([OH:23])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 5615061-Benzyl-2,5-dihydropyrroleHCID 10942334Sodium Methoxide

Product 1

HCID 9855817HCID 9855817, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 15.9 g (0.1 mol) of 1-benzyl-3-pyrroline, 12.0 g (0.12 mol) of 98% sulfuric acid, and 60.0 g of acetone in a quartz round flask reactor, 45.6 g (0.20 mol) of (NH4)2S2O8 (ammonium peroxydisulfate produced by Mitsubishi Gas Chemical Industry Co., Ltd.) was added with stirring and allowed to react for 5 days at room temperature with irradiation by 500W Xe lamps (UXL-500D xenon lamp produced by Ushio). 57.9 g (0.3 mol) of 28 wt % NaOMe in methanol solution (produced by Katayama Chemical Industry Co., Ltd.) was continuously added to the reaction mixture and stirred for 5 hours under reflux. After completion, acetone and methanol were evaporated under reduced pressure, and extracted with toluene and water. After the solvent was evaporated under reduced pressure, 15.8 g of 1-benzyl-4-methoxy-3-pyrrolidinol (yield 76.0%) was obtained.

Workup

  1. stirringstirred for 5 hours
  2. temperatureunder reflux
  3. customAfter completion, acetone and methanol were evaporated under reduced pressure
  4. extractionextracted with toluene and water
  5. customAfter the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6a7f303e719743c09995443d1ff45bce
Source dataset
uspto-grants-2002_11
Patent number
US06479668B1

Reaction notes

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