4-Fluorobenzaldehyde → HCID 53917358, compound

HRID 2293876Notes

Reaction equation

HRID 2293876 reaction equation
[O-]CC.[Na+].[F:5][C:6]1[C:11]([C:12](=[O:14])[CH3:13])=[C:10]([F:15])[C:9]([F:16])=[C:8]([F:17])[C:7]=1[F:18].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1>C(O)C.CCOCC>[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[CH:13][C:12]([C:11]2[C:6]([F:5])=[C:7]([F:18])[C:8]([F:17])=[C:9]([F:16])[C:10]=2[F:15])=[O:14])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 695462',3',4',5',6'-PentafluoroacetophenoneHCID 2723922Sodium ethoxide

Product 1

HCID 53917358HCID 53917358, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of sodium ethoxide (21% in EtOH, 0.32 gm, 4.76 mmol) was added to a mixture of 1-(pentafluorophenyl)-1-ethanone (5.91 gm, 47.6 mmol, Aldrich) and 4-fluorobenzaldehyde (10.00 gm, 47.6 mmol) stirring in ethanol (100 ml) under argon. The solution was allowed to stir at room temperature for 18 hours, then EtOH was evaporated to afford a yellowish, oily solid. The solid was redissolved in ether, washed with water and brine, then dried over MgSO4, filtered and concentrated to give a yellow residue. The residue was purified by flash chromatography on Merck silica gel in 5% EtOAc/hexane. Fractions containing the product were combined and concentrated to a yellow solid. The solid was recrystallized from hexane to afford the title compound as large yellow crystals (8.220 gm, 52%).

Workup

  1. customEtOH was evaporated
  2. customto afford a yellowish, oily solid
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a yellow residue
  8. customThe residue was purified by flash chromatography on Merck silica gel in 5% EtOAc/hexane
  9. additionFractions containing the product
  10. concentrationconcentrated to a yellow solid
  11. customThe solid was recrystallized from hexane

Sources & evidence

ORD record
ord-8f5ea78364c34a92b8794badf6d5977f
Source dataset
uspto-grants-1997_11
Patent number
US05686433

Reaction notes

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