Water → HCID 22032251, compound

HRID 1792450Notes

Reaction equation

HRID 1792450 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[H-].[Na+].F[C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C:16](=[O:18])[CH3:17].O>O1CCCC1>[F:15][C:13]1[CH:12]=[CH:11][C:10]([C:16](=[O:18])[CH3:17])=[C:9]([O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 677702,4-Difluoroacetophenone

Product 1

HCID 22032251HCID 22032251, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 1.75 g 2-methoxy ethanol in tetrahydrofuran (23 mL) was added dropwise to a suspension of 0.84 g of 60% sodium hydride in tetrahydrofuran (21 mL), and subsequently a solution of 3.0 g 2′,4′-difluoroacetophenone in tetrahydrofuran (19 mL) was added dropwise thereto. The temperature of the mixture was increased to room temperature, then the mixture was stirred for 24 hours, water was carefully added thereto, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate, the solvent was removed, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 2.84 g of the title compound (yellow oil).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed
  5. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f1c2816f2f184ef9a353812df19c64f4
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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