4-t-Butoxy-3-chloro-2,5,6-trifluoropyridine → 4-t-Butoxy-2,3,6-trifluoropyridine

HRID 1600995

반응식

HRID 1600995 반응식
[C:1]([O:5][C:6]1[C:11]([F:12])=[C:10]([F:13])[N:9]=[C:8]([F:14])[C:7]=1Cl)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]1[CH:7]=[C:8]([F:14])[N:9]=[C:10]([F:13])[C:11]=1[F:12])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 108575794-t-Butoxy-3-chloro-2,5,6-trifluoropyridineHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 106085474-t-Butoxy-2,3,6-trifluoropyridine수율 56,470.898%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 887Methanol용매

실험 절차

To 4-t-butoxy-3-chloro-2,5,6-trifluoropyridine (24.92 g, 0.104 mmol) in 100 mL of methanol was added 2.5 g of Pearlman's catalyst (Aldrich Chemical Co.), and the mixture was stirred at ambient temperature for 14 hours under and atmosphere of hydrogen. An additional 2.5 g of catalyst was added, and the mixture was stirred for another 22 hours. The mixture was filtered, the filtrate was concentrated, and the residue was extracted with hexane/ether. After filtration, the solvent was removed by evaporation, and the residue was purified by flash chromatography (ethyl acetate:hexane 1:16) to yield 12.05 g of 4-t-butoxy-2,3,6-trifluoropyridine. MS 206 (M+H)+, 233 (M+18)+ ; 1H NMR (CDCl3)∂: 1.52 (s, 9H), 6.5 (m, 1H); 19F NMR (CDCl3, CFCl3 as reference)∂: 72.60 (dd, J1 =14.3, J2 =21.0 Hz), 89.74 (dd, J1 =14.3, J2 =21.0 Hz), 164.68 (dt, J1 =4.2, J2 =21.0 Hz).

후처리

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. extractionthe residue was extracted with hexane/ether
  4. filtrationAfter filtration
  5. customthe solvent was removed by evaporation
  6. customthe residue was purified by flash chromatography (ethyl acetate:hexane 1:16)

출처 및 근거

ORD 기록
ord-a114a9ea48c343e39f533457a6f464c2
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05977133

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