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Aluminium lithium hydride → (6-(2,2,2-Trifluoroethoxy)pyridin-2-yl)methanol

HRID 715390
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HRID 715390 반응식
[F:1][C:2]([F:16])([F:15])[CH2:3][O:4][C:5]1[N:10]=[C:9]([C:11](OC)=[O:12])[CH:8]=[CH:7][CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:16][C:2]([F:1])([F:15])[CH2:3][O:4][C:5]1[N:10]=[C:9]([CH2:11][OH:12])[CH:8]=[CH:7][CH:6]=1
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참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 67510684Methyl 6-(2,2,2-trifluoroethoxy)picolinate

생성물 1

HCID 62240732(6-(2,2,2-Trifluoroethoxy)pyridin-2-yl)methanol수율 92%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of methyl 6-(2,2,2-trifluoroethoxy)picolinate (0.40 g, 1.69 mmol, Step-2) in THF (17 mL) is added slowly lithium aluminum hydride (0.096 g, 2.53 mmol) at 0° C. The resulting mixture is stirred at rt for 1 hour. The reaction mixture is carefully quenched with 25% aqueous ammonia solution at 0° C. Then the mixture is diluted with DCM (50 mL) and celite is added to the mixture. After stirring at rt for 1 hour, the mixture is filtrated through a pad of celite, and the filtrate is concentrated in vacuo to give 0.32 g (92% yield) of the title compound as white solid. This material is used for the next reaction (Step-4) without further purification.

후처리

  1. customThe reaction mixture is carefully quenched with 25% aqueous ammonia solution at 0° C
  2. additionThen the mixture is diluted with DCM (50 mL) and celite
  3. additionis added to the mixture
  4. stirringAfter stirring at rt for 1 hour
  5. filtrationthe mixture is filtrated through a pad of celite
  6. concentrationthe filtrate is concentrated in vacuo

출처 및 근거

ORD 기록
ord-422dd8f065d8477387161ddc3c0276a4
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09187475B2

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