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

HRID 1160066ノート

反応式

HRID 1160066 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-741f05c9bb32419a947e9a667e4177d0
出典データセット
uspto-grants-2010_10
特許番号
US07816344B2

反応ノート

読み込み中…