Thiophenol → HCID 22042388, compound

HRID 1790883Notes

Reaction equation

HRID 1790883 reaction equation
[CH3:1][C:2]1([C:7]2([CH2:10][CH2:11]OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4][O:3]1.[C:23]1([SH:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[CH3:1][C:2]1([C:7]2([CH2:10][CH2:11][S:29][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:8][CH2:9]2)[O:3][CH2:4][CH2:5][O:6]1

Participants

4

Reactant 2

HCID 7969ThiophenolHCID 17910741HCID 17910741, compound

Product 1

HCID 22042388HCID 22042388, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

590 mg of 10 is dissolved in 2 ml of dimethylformamide (DMF) and added under nitrogen to a mixture of 300 mg of potassium-t-butylate and 0.27 ml of thiophenol in 5 ml of DMF. It is stirred for 1 hour at room temperature and then quenched with sodium chloride solution. It is extracted with ethyl acetate, washed with sodium bicarbonate solution and sodium chloride solution, dried on sodium sulfate, concentrated by evaporation, and the residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 630 mg of title compound 11 accumulates as a yellowish oil.

Workup

  1. customquenched with sodium chloride solution
  2. extractionIt is extracted with ethyl acetate
  3. washwashed with sodium bicarbonate solution and sodium chloride solution
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customthe residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 630 mg of title compound 11 accumulates as a yellowish oil

Sources & evidence

ORD record
ord-1ecf1a0e096f46bc8ab8d467c091a4ea
Source dataset
uspto-grants-2006_07
Patent number
US07071344B1

Reaction notes

Loading…