Furfural → HCID 68954860, compound

HRID 1971269Notes

Reaction equation

HRID 1971269 reaction equation
O1C=CC=C1C=O.[OH-].[K+].[N+](C[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=O)#[C-].[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C@@H:25]1[O:29][CH:28]=[N:27][C@H:26]1[C:30]([N:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1)=[O:31]>CO>[CH:16]1[C:17]2[C:22](=[CH:23][CH:24]=[CH:19][CH:18]=2)[C:21]([C@@H:25]2[O:29][CH:28]=[N:27][C@H:26]2[C:30]([N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)=[O:31])=[CH:13][N:15]=1.[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C@@H:25]1[O:29][CH:28]=[N:27][C@H:26]1[C:30]([N:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1)=[O:31]

Participants

7

Reactant 4

HCID 7362FurfuralHCID 14797Potassium HydroxideHCID 6455476Pyrrolidine, 1-(isocyanoacetyl)-HCID 68954860HCID 68954860, compound

Product 2

HCID 68954846HCID 68954846, compoundHCID 68954860HCID 68954860, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

BLE 04136C 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, 5.43 mmol). After work-up the residue was purified by column chromatography on silica (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 04136D as a yellow pale oil (0.742 g, 58.5% yield).

Workup

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

Sources & evidence

ORD record
ord-edc07d4a863e457f9d511a22430c5dc6
Source dataset
uspto-grants-2013_04
Patent number
US08431599B2

Reaction notes

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