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

HRID 1160066Notes

Reaction equation

HRID 1160066 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-741f05c9bb32419a947e9a667e4177d0
Source dataset
uspto-grants-2010_10
Patent number
US07816344B2

Reaction notes

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