Water → HCID 67753650, compound

HRID 486735Notes

Reaction equation

HRID 486735 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][CH2:9][CH2:8][CH:7]=1)=[O:5])[CH3:2].[C-:11]#[N:12].[Na+].O>CN(C)C=O>[C:11]([C@H:7]1[C@H:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[S:10][CH2:9][CH2:8]1)#[N:12]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 19096346HCID 19096346, compound

Product 1

HCID 67753650HCID 67753650, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-ethoxycarbonyl-2,3-dihydrothiophene (500 mg) in dimethylformamide (3 ml), sodium cyanide (187 mg) was added under nitrogen atmosphere and the mixture was stirred for 2 days at room temperature. Water was added to the mixture and extracted with diethyl ether. The organic layer was washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 130 mg (24%) of trans-4-cyano-5-ethoxycarbonyltetrahydrothiophene.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-2b57834ab84c4a95bf7fb380e7d0a817
Source dataset
uspto-grants-1994_03
Patent number
US05292767

Reaction notes

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