Water → Methyl 4-cyano-2,5-dihydro-3-furancarboxylate

HRID 30201Notes

Reaction equation

HRID 30201 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH:9]([C:10]#[N:11])[CH2:8][O:7][CH2:6]1)=[O:4].O=S(Cl)Cl.O>N1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH2:6][O:7][CH2:8][C:9]=1[C:10]#[N:11])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 86590090Methyl 4-cyanooxolane-3-carboxylate

Product 1

HCID 45090151Methyl 4-cyano-2,5-dihydro-3-furancarboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Cyano-tetrahydro furane 3-carboxylic acid methyl ester was dissolved in 4.9 ml of pyridine and treated with 4.4 ml (60 mmol) of SOCl2 during 90 min under nitrogen at 4° C. The resulting solution was warmed to room temperature, stirred for 6 hours and poured into 40 ml water at 4° C. and extracted with benzene. Combined extracts were dried and concentrated in vacuo to give 90% yield of 4-cyano-2,5-dihydro furane 3-carboxylic acid methyl ester.

Workup

  1. extractionextracted with benzene
  2. customCombined extracts were dried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-690d8c570e1a46329a94aa97ac35f144
Source dataset
uspto-grants-2008_09
Patent number
US07423057B2

Reaction notes

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