Sulfuric Acid → Methyl 4-cyanooxolane-3-carboxylate

HRID 30200Notes

Reaction equation

HRID 30200 reaction equation
[C-:1]#[N:2].[K+].[CH3:4][O:5][C:6]([CH:8]1[C:12](=O)[CH2:11][O:10][CH2:9]1)=[O:7].OS(O)(=O)=O>O.CCOCC>[CH3:4][O:5][C:6]([CH:8]1[CH:12]([C:1]#[N:2])[CH2:11][O:10][CH2:9]1)=[O:7]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 9032Potassium CyanideHCID 14666564Methyl 4-oxooxolane-3-carboxylate

Product 1

HCID 86590090Methyl 4-cyanooxolane-3-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 3.9 g (60 mmol) KCN in 5.5 ml of water at 4° C., a solution of 2.9 g (20 mmol) of 4-oxo-tetrahydro furane 3-carboxylic acid methyl ester in ether (26 ml) was added. To the precipitate of salts, 3.5 ml H2SO4 (18 N) was added and stirred for 16 hours. Then the organic solution was separated, the salts were washed twice with benzene, dried over sodium sulfate and concentrated in vacuo to give 4-cyano-tetrahydro furane 3-carboxylic acid methyl ester.

Workup

  1. customThen the organic solution was separated
  2. washthe salts were washed twice with benzene
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9274e00d4d174b7d9c1bd6c9718ddb6b
Source dataset
uspto-grants-2008_09
Patent number
US07423057B2

Reaction notes

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