Sodium Thiosulfate → 4-(phenyl-2-thienylmethyl)Pyridine

HRID 400294Notes

Reaction equation

HRID 400294 reaction equation
[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O-]S([O-])(=S)=O.[Na+].[Na+]>CC#N>[C:1]1([CH:7]([C:14]2[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=2)[C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24477Sodium ThiosulfateHCID 15525589(Phenyl)-pyrid-4-yl-(thien-2-yl)methanol

Product 1

HCID 155255854-(phenyl-2-thienylmethyl)Pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

NAI (2.27 g, 16.0 mmol) and Me3Sicl (2.02, 16.0 mmol) were stirred in CH3CN (70 mL) at 0° C. (Phenyl)-pyrid-4-yl-(thien-2-yl)methanol (0.534 g, 2.00 mmol (Example 93)) was added at 0° C. and the resulting solution was stirred over night at room temperature. Na2S2O3 (sat., 20 mL) was added and the two phase system was stirred 5 minutes. The phases were separated and the organic layer was dried (MgSO4), filtered and evaporated. The resulting crystals were dissolved in CH2Cl2 (30 mL), the solution was washed with NaHCO3 (30 mL, sat.) and H2O (30 mL), dried (MgSO4) and evaporated yielding 0.41 g which was recrystallized in diisopropyl ether giving 0.22 g (43.8%) of the pure title compound.

Workup

  1. additionwas added at 0° C.
  2. stirringthe two phase system was stirred 5 minutes
  3. customThe phases were separated
  4. dry with materialthe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe resulting crystals were dissolved in CH2Cl2 (30 mL)
  8. washthe solution was washed with NaHCO3 (30 mL, sat.) and H2O (30 mL)
  9. dry with materialdried (MgSO4)
  10. customevaporated
  11. customyielding 0.41 g which
  12. customwas recrystallized in diisopropyl ether giving 0.22 g (43.8%) of the pure title compound

Sources & evidence

ORD record
ord-dd4992cda33d43fc886e61ed003e2b5f
Source dataset
uspto-grants-1998_10
Patent number
US05827501

Reaction notes

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