Hydrochloric Acid → 2,2,2-Trifluoro-1-(pyridin-2-yl)ethan-1-ol

HRID 2041319노트

반응식

HRID 2041319 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[O:8].[F:9][C:10]([Si](C)(C)C)([F:12])[F:11].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>C1COCC1.[OH-].[Na+]>[OH:8][CH:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:10]([F:12])([F:11])[F:9]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 142732-PyridinecarboxaldehydeHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride

생성물 1

HCID 137429262,2,2-Trifluoro-1-(pyridin-2-yl)ethan-1-ol수율 93.2%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran촉매HCID 8028Tetrahydrofuran용매HCID 14798Sodium Hydroxide용매

반응 조건

온도
0 °C

실험 절차

To a stirred solution of 2-pyridine carboxaldehyde (2.09 g, 19.5 mmol) and (trifluoromethyl)trimethylsilane (3.33 g, 23.4 mmol) in THF (30 mL) at 0° C. add 1M tetrabutylammonium fluoride in THF (956 μl, 0.956 mmol). Continue stirring for 30 min at 0° C. and then at ambient temperature for 2 h. Add 1M aqueous HCl (20 mL) and stir 2 h at ambient temperature. Dilute with aqueous 1M aqueous NaOH to pH 8, extract the mixture three times with EtOAc, dry over anhydrous Na2SO4, and concentrate in vacuo. Purify by chromatography eluting with hexane/EtOAc (8:2) to give the desired intermediate as a yellow oil (3.22 g, 93%).

후처리

  1. waitat ambient temperature for 2 h
  2. stirringstir 2 h at ambient temperature
  3. extractionextract the mixture three times with EtOAc
  4. dry with materialdry over anhydrous Na2SO4
  5. concentrationconcentrate in vacuo
  6. customPurify by chromatography
  7. washeluting with hexane/EtOAc (8:2)

출처 및 근거

ORD 기록
ord-b33d811f9a2249cd8ee36f2a0da13f6f
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580780B2

반응 노트

불러오는 중…