Tetrahydrofuran → HCID 44754915, compound

HRID 1666098Notes

Reaction equation

HRID 1666098 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:5]=1[CH:6]=O.[OH:13]S([O-])(=O)=O.[Na+].[CH2:19]1[CH2:23][O:22][CH2:21][CH2:20]1>CC(=O)OCC>[CH2:21]([O:22][C:23](=[O:13])/[CH:19]=[CH:6]/[C:5]1[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:4]=1[F:3])[CH3:20]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 1376632,5-DifluorobenzaldehydeHCID 516919Sodium Bisulfate

Product 1

HCID 44754915HCID 44754915, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To an iced chilled suspension of NaH (1.13 g, 60% in oil dispersion, 28.2 mmol) in THF (32 mL) was added triethylphosphonoacetate (5.6 ml, 28.2 mmol). The reaction mixture was stirred at rt for 20 min. 2,5-difluoro-benzaldehyde (3.34 g, 23.5 mmol) was added drop wise. After 30 min, 10% aq. NaHSO4 (100 mL) was added and the mixture was diluted with EA (150 mL). The two phases were separated and the aq. layer was extracted twice with EA (2×100 mL). The combined org. layers were washed with brine (100 mL), dried over Na2SO4, filtered and concentrated to dryness. The residue was chromatographed over SiO2 (Hex-EA 19-1) to afford the title ester (5.0 g, 100% yield) as a colourless oil.

Workup

  1. waitAfter 30 min
  2. customThe two phases were separated
  3. extractionthe aq. layer was extracted twice with EA (2×100 mL)
  4. washlayers were washed with brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was chromatographed over SiO2 (Hex-EA 19-1)

Sources & evidence

ORD record
ord-b93423e74ed5413597c05c3e7ade03b5
Source dataset
uspto-grants-2011_10
Patent number
US08044044B2

Reaction notes

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