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

HRID 2060615노트

반응식

HRID 2060615 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>[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

5

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 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

6-Bromopyridine-2-carbaldehyde (1.0 g, 5.38 mmol) was dissolved 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 ice bath was removed and the reaction was stirred for 4.5 hours at room temperature. The reaction was then diluted with water and brine and extracted with ethyl acetate three times. 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. 1H NMR (600 MHz, d6-DMSO) δ 7.83 (m, 1H), 7.67 (d, 1H), 7.63 (d, 1H), 7.15 (d, 1H), 5.11 (m, 1H).

후처리

  1. customThe ice bath was removed
  2. additionThe reaction was then diluted with water and brine
  3. extractionextracted with ethyl acetate three times
  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-955fb7fdd92c498b9c2686b54f34ef49
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278335B2

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