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

HRID 2041319ノート

反応式

HRID 2041319 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran触媒HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-b33d811f9a2249cd8ee36f2a0da13f6f
出典データセット
uspto-grants-2013_11
特許番号
US08580780B2

反応ノート

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