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

HRID 70517노트

반응식

HRID 70517 반응식
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

참가 물질

5

반응물 4

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

생성물 1

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

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온도
60 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-189c5c873f8b44be9ba1929914513cd3
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822503B2

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