(Trifluoromethyl)trimethylsilane → 1-(6-Bromopyridin-2-yl)-2,2,2-trifluoroethan-1-ol

HRID 385986노트

반응식

HRID 385986 반응식
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[Si]([C:14]([F:17])([F:16])[F:15])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O.[Cl-].[Na+].O>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:9])[C:14]([F:17])([F:16])[F:15])[CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 27570096-Bromopyridine-2-carbaldehyde

생성물 1

HCID 583352521-(6-Bromopyridin-2-yl)-2,2,2-trifluoroethan-1-ol

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
0 °C

실험 절차

6-Bromopyridine-2-carbaldehyde (1.0 g, 5.38 mmol) was taken up in 35 mL THF and cooled to 0° C. TMSCF3 (1.0 mL, 6.45 mmol) was added followed by tetrabutylammonium fluoride (6.45 mL of 1.0M in THF). The reaction was stirred allowed to warm to room temperature and maintained at that temperature for 4.5 hours. The mixture was then diluted with water and brine, and extracted with ethyl acetate (3×). The organic layers were combined and dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography (0-40% ethyl acetate/hexanes) afforded the title compound.

후처리

  1. temperatureto warm to room temperature
  2. temperaturemaintained at that temperature for 4.5 hours
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by silica gel chromatography (0-40% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-c027576ca8d34dd3b7e6acf0e1e723d2
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

반응 노트

불러오는 중…