Furfural → 1-Pyrrolidinecarboxaldehyde

HRID 1423885Notes

Reaction equation

HRID 1423885 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7].[OH-].[K+].[N+:10]([CH2:12][C:13]([N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:14])#[C-:11]>CO>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C@@H:6]1[O:7][CH:11]=[N:10][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:14].[N:15]1([CH:13]=[O:14])[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 7362FurfuralHCID 14797Potassium HydroxideHCID 6455476Pyrrolidine, 1-(isocyanoacetyl)-

Product 2

HCID 773721-PyrrolidinecarboxaldehydeYield 276.2%HCID 68954860HCID 68954860, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

BLE 04136D was prepared in accordance with method D using 2-furaldehyde (0.449 mL, 5.42 mmol), KOH (0.276 mg, 4.92 mmol) in methanol (5 mL) and 2-isocyano-1-(pyrrolidin-1-yl)ethanone BLE 04098 (0.75 g, 5.42 mmol). After work-up the residue was purified by column chromatography (SiO2, cyclohexane:EtOAc=100:0 to 0:100) to led, after evaporation, to trans-5-(furan-2-yl)-4,5-dihydrooxazol-4-yl)(pyrrolidin-1-yl)methanone BLE 04138D (0.742 g, 58.5% yield) as a pale yellow oil.

Workup

  1. customAfter work-up the residue was purified by column chromatography (SiO2, cyclohexane:EtOAc=100:0 to 0:100)
  2. customafter evaporation

Sources & evidence

ORD record
ord-4686be6eba5b4f73af03ee9c2141df9c
Source dataset
uspto-grants-2015_01
Patent number
US08927589B2

Reaction notes

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