Triethylamine → HCID 11645580, compound

HRID 2245808Notes

Reaction equation

HRID 2245808 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:11]=[C:12]([CH2:16]O)[CH:13]=[CH:14][CH:15]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.N1C=CC=CC=1.S(=O)(=O)=O.[CH2:36]([O:38][C:39](=[O:60])[CH:40]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:37]>CS(C)=O.ClCCl.C(OCC)(=O)C.O>[CH2:36]([O:38][C:39](=[O:60])/[CH:40]=[CH:16]/[C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([S:9][C:6]2[CH:7]=[CH:8][C:3]([N:2]([CH3:18])[CH3:1])=[CH:4][CH:5]=2)[CH:11]=1)[CH3:37]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 168533Sulfur trioxide-pyridineHCID 11615861HCID 11615861, compound

Product 1

HCID 11645580HCID 11645580, compoundYield 74.8%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3-(4-dimethylamino-phenylsulfanyl)-phenyl)-methanol (255 mg, 0.98 mmol) and triethylamine (1.3 mL, 9.2 mmol) in dimethyl sulfoxide (5 mL) was added a solution of pyridine-sulphur trioxide (469 mg, 2.95 mmol) in dimethyl sulfoxide (5 mL). The mixture was stirred for 1 hour at room temperature and water (20 mL) and ethyl acetate (40 mL) were added. The organic layer was washed with water (3×10 mL) and brine (20 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a colourless oil. This oil was dissolved in dichloromethane (10 mL) and (triphenylphosphoranylidene)-acetic acid ethyl ester (700 mg, 2.0 mmol) was added. The mixture was stirred at reflux for 3 hours and concentrated under reduced pressure. The residue was purified by flash chromatography (20:80:1 ethyl acetate:40-60° C. petroleum ether:triethylamine) to give the title compound as a colourless oil (240 mg, 74%).

Workup

  1. washThe organic layer was washed with water (3×10 mL) and brine (20 mL)
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give a colourless oil
  6. stirringThe mixture was stirred
  7. temperatureat reflux for 3 hours
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (20:80:1 ethyl acetate:40-60° C. petroleum ether:triethylamine)

Sources & evidence

ORD record
ord-1f8248bfa3e3472a9b11940491e43d97
Source dataset
uspto-grants-2010_03
Patent number
US07683185B2

Reaction notes

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