Thioanisole → HCID 19347976, compound

HRID 1637194Notes

Reaction equation

HRID 1637194 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:16]([S:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:18])=[C:15]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[S:14][C:13]=2[CH:30]=1)C1C=CC=CC=1.C1(SC)C=CC=CC=1>FC(F)(F)C(O)=O>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[C:16]([S:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:18])=[C:15]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[S:14][C:13]=2[CH:30]=1

Participants

4

Reactant 2

HCID 7520ThioanisoleHCID 19348001HCID 19348001, compound

Product 1

HCID 19347976HCID 19347976, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trifluoroacetic acid (50 ml) was added to a stirred mixture of ethyl 6-(benzyloxy)-3-(phenylsulfinyl)benzo[b]thiophene-2-carboxylate (Example 31, 4.9 g, 11.2 mmol) and methyl phenyl sulfide (5.2 ml, 45 mmol) at ambient temperature under a nitrogen atmosphere. After 20 hours the solvents were removed under reduced pressure, and the residue was azeotroped using toluene. The residue was flash chromatographed on silica gel using 2% ethanol in dichloromethane as eluant. The isolated product was crystallised from diisopropyl ether to give the title compound as a colourless solid (3.05 g).

Workup

  1. customAfter 20 hours the solvents were removed under reduced pressure
  2. customthe residue was azeotroped
  3. customchromatographed on silica gel using 2% ethanol in dichloromethane as eluant
  4. customThe isolated product was crystallised from diisopropyl ether

Sources & evidence

ORD record
ord-23704c86b2704c188fde81901c918d2a
Source dataset
uspto-grants-2000_03
Patent number
US06040309

Reaction notes

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