Sodium hydride → 2-Bromo-3-[3-(tetrahydropyran-2-yloxy)propoxy]benzaldehyde

HRID 339618노트

반응식

HRID 339618 반응식
[Br:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH2:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1.[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[C:9]([O:10][CH2:12][CH2:13][CH2:14][O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 37146742-Bromo-3-hydroxybenzaldehyde

생성물 1

HCID 574292492-Bromo-3-[3-(tetrahydropyran-2-yloxy)propoxy]benzaldehyde수율 102%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-bromo-3-hydroxybenzaldehyde (5.18 g, 25.0 mmol) and 2-(3-bromopropoxy)tetrahydro-2H-pyran (5.1 mL, 30 mmol) in DMF (60 mL) was added sodium hydride (1.20 g, 30.0 mmol) at 0° C. under nitrogen atmosphere, and the mixture was stirred at room temperature for overnight. The reaction was quenched with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water twice and brine, and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (9:1 to 3:1 hexane/ethyl acetate) to give 2-bromo-3-[3-(tetrahydropyran-2-yloxy)propoxy]benzaldehyde (8.75 g, quantitative).

후처리

  1. customThe reaction was quenched with water
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water twice
  4. dry with materialbrine, and dried on anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (9:1 to 3:1 hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-8df62a3a8b0f4649865312acb2fcbbda
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895534B2

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