Sodium Chloride → 2-(4-Fluorophenyl)-2-methyl-5-[2-(3-thienyl)ethenyl]-3(2H)-furanone

HRID 1085590

Reaction equation

HRID 1085590 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[CH:2]1.[CH3:8][C:9]1([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[C:13](=[O:14])[CH:12]=[C:11]([CH3:15])[O:10]1.[OH-].[Na+].[Cl-].[Na+]>C(O)C>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:9]2([CH3:8])[C:13](=[O:14])[CH:12]=[C:11]([CH:15]=[CH:6][C:3]3[CH:4]=[CH:5][S:1][CH:2]=3)[O:10]2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 681353-ThiophenecarboxaldehydeHCID 150867042-(4-Fluorophenyl)-2,5-dimethylfuran-3(2H)-one

Product 1

HCID 536992992-(4-Fluorophenyl)-2-methyl-5-[2-(3-thienyl)ethenyl]-3(2H)-furanoneYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-thiophenecarboxaldehyde (1.3 g, 1.2 mM) and 2,5-dimethyl-2-(4-fluorophenyl)-3(2H)-furanone (2.0 g, 9.8 mM) in ethanol (75 mL), was added 1N aqueous sodium hydroxide (2 mL, 2 mM). The reaction solution was stirred at room temperature for one day. After saturated aqueous sodium chloride (400 mL) was added, the aqueous layer was extracted with dichloromethane (3×100 mL). The combined dichloromethane extracts were washed with saturated aqueous sodium chloride (50 mL), dried over MgSO4, filtered and concentrated to give a brown oil. The crude product was purified by chromatography (silica gel, pet. ether-ethyl acetate) to afford a yellow solid (1.8 g, 62% yield), m.p. 97°-98° C.

Workup

  1. extractionthe aqueous layer was extracted with dichloromethane (3×100 mL)
  2. washThe combined dichloromethane extracts were washed with saturated aqueous sodium chloride (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a brown oil
  7. customThe crude product was purified by chromatography (silica gel, pet. ether-ethyl acetate)

Sources & evidence

ORD record
ord-cd62e6827dc34d918bb82858a1d33eb2
Source dataset
uspto-grants-1991_04
Patent number
US05010102

Linked notes

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