Water → HCID 54047018, compound

HRID 1740272Notes

Reaction equation

HRID 1740272 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1(S)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(OC(=O)C(Cl)(Cl)CC[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][Br:31])C.O>CN(C)C=O>[Br:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH:22]=[CH:21][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 15338401HCID 15338401, compound

Product 1

HCID 54047018HCID 54047018, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.46 g (25.0 mmol) potassium carbonate and 2.75 g (25.0 mmol) thiophenol were added to a solution of 10.1 g (25.0 mmol) 3 in 200 ml dimethylformamide. It was stirred for 12 h at room temperature, 300 ml water was added, it was extracted with ether, washed with water, dried over sodium sulfate and the solvent was removed on a rotary evaporator. 6.62 g (61%) 66 was obtained as a nearly colourless oil after flash chromatography of the residue (silica gel, heptane/toluene 5:1).

Workup

  1. extractionit was extracted with ether
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-0155b7c84af14c45968578216c2f8423
Source dataset
uspto-grants-1999_10
Patent number
US05968982

Reaction notes

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