Citric Acid → trans-5-Tert-butoxycarbonyl-2-cyanomethyltetrahydrothiophene

HRID 486723Notes

Reaction equation

HRID 486723 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[S:12][C@@H:11]([CH2:13]Cl)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-:15]#[N:16].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[C:1]([O:5][C:6]([C@@H:8]1[S:12][C@@H:11]([CH2:13][C:15]#[N:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 8929Sodium CyanideHCID 54302749HCID 54302749, compound

Product 1

HCID 54384892trans-5-Tert-butoxycarbonyl-2-cyanomethyltetrahydrothiophene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of trans-5-tert-butoxycarbonyl-2-chloromethyltetrahydrothiophene (3.5 g) in dimethylformamide (15 ml), sodium cyanide (1.5 g) is added and the mixture was stirred for 5 hours at 60°-70° C. 5% aqueous citric acid solution is added to the mixture and extracted with ethyl acetate - benzene (1:1). The organic layer is washed with water and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue is purified by a silica gel column chromatography to give trans-5-tert-butoxycarbonyl-2-cyanomethyltetrahydrothiophene.

Workup

  1. extractionextracted with ethyl acetate - benzene (1:1)
  2. washThe organic layer is washed with water and saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe oily residue is purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-1f2bd5911a09409c8ab71883b0189bc6
Source dataset
uspto-grants-1994_03
Patent number
US05292767

Reaction notes

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