Water → HCID 54425106, compound

HRID 443051Notes

Reaction equation

HRID 443051 reaction equation
[C:1]([C:3]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:4][CH2:5][CH2:6]I)#[N:2].C(=O)([O-])[O-].[K+].[K+].[C:26]([O:30][CH2:31][CH3:32])(=[O:29])[CH2:27][SH:28].O>CN(C)C=O>[C:1]([C:3]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:4][CH2:5][CH2:6][S:28][CH2:27][C:26]([O:30][CH2:31][CH3:32])=[O:29])#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 86754050HCID 86754050, compound

Product 1

HCID 54425106HCID 54425106, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-cyano-4,4-diphenyl iodobutane (0.4 g, 1.1 mmol.) in N,N-dimethylformamide (3 ml) were added potassium carbonate (0.31 g, 2,2 mmol.) and ethyl thioglycolate (0.14 g, 1.2 mmol.). The mixture was stirred for 15 hours at room temperature. To the reaction mixture was added water, which was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was subjected to a silica gel column chromatography, eluting with hexane - ethyl acetate (4:1) to afford the title compound (0.22 g).

Workup

  1. extractionwas subjected to extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous saline solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. washeluting with hexane - ethyl acetate (4:1)

Sources & evidence

ORD record
ord-4f13273d3cac4ee698380fd6a5f179ad
Source dataset
uspto-grants-1999_04
Patent number
US05891916

Reaction notes

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