Trifluoroacetic acid → 2-Methoxy-3-methyl-6-[4-(methylsulfanyl)benzyl]pyridine

HRID 70517Notes

Reaction equation

HRID 70517 reaction equation
C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[CH3:15][O:16][C:17]1[N:22]=[C:21]([CH:23]([C:25]2[CH:30]=[CH:29][C:28]([S:31][CH3:32])=[CH:27][CH:26]=2)O)[CH:20]=[CH:19][C:18]=1[CH3:33].C(=O)(O)[O-].[Na+]>>[CH3:15][O:16][C:17]1[C:18]([CH3:33])=[CH:19][CH:20]=[C:21]([CH2:23][C:25]2[CH:26]=[CH:27][C:28]([S:31][CH3:32])=[CH:29][CH:30]=2)[N:22]=1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 67397903(6-Methoxy-5-methylpyridin-2-yl)[4-(methylsulfanyl)phenyl]methanol

Product 1

HCID 584525372-Methoxy-3-methyl-6-[4-(methylsulfanyl)benzyl]pyridine

Conditions

Temperature
60 °C

Procedure

Triethylsilane (5 mL) and trifluoroacetic acid (5 mL) were sequentially added to (6-methoxy-5-methylpyridin-2-yl)[4-(methylsulfanyl)phenyl]methanol obtained in Reference Example 1-36(2) (2.13 g), and the mixture was stirred at 60° C. for four hours. The reaction solution was poured into saturated aqueous sodium bicarbonate, followed by extraction with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→4:1→2:1) to give the title compound as a colorless oil (1.69 g).

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→4:1→2:1)

Sources & evidence

ORD record
ord-189c5c873f8b44be9ba1929914513cd3
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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