Furfural → HCID 21221461, compound

HRID 1585072Notes

Reaction equation

HRID 1585072 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[CH3:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=[O:10].C[O-].[Na+]>CO>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:9](=[O:10])[CH2:8][CH2:6][C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 7362FurfuralHCID 98284'-FluoroacetophenoneHCID 10942334Sodium Methoxide

Product 1

HCID 21221461HCID 21221461, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-furaldehyde (4.15 ml, 50 mmol) and 4-fluoroacetophenone (6.16 ml, 50 mmol) in methanol (200 ml), sodium methoxide (2.85 g, 50 mmol) was added. After stirring at room temperature for 18 hours, the reaction mixture was concentrated, resuspended in ethyl acetate (600 ml) and diluted with water. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated. The crude solid (10.27 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 7/3) to give 1-(4-fluorophenyl)-3-(2-furanyl)propan-1-one (8.9 g, 95%) as a white solid: mp (DSC) 72° C. Anal Calc'd. for C13H10FO: C, 72.22; H, 4.20. Found: C, 72.18; H, 4.38.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additiondiluted with water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude solid (10.27 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 7/3)

Sources & evidence

ORD record
ord-e78ebdeeb63d4b4abf81190f47736238
Source dataset
uspto-grants-1999_08
Patent number
US05935990

Reaction notes

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