Water → 2-(4-Fluorophenyl)furan

HRID 414646Notes

Reaction equation

HRID 414646 reaction equation
[O:1]1[CH2:5][C:2]1([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[C:3]#[CH:4].O>OS(O)(=O)=O.C(O)C>[F:12][C:9]1[CH:8]=[CH:7][C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 962WaterHCID 14424685HCID 14424685, compound

Product 1

HCID 116152232-(4-Fluorophenyl)furanYield 58%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 0.7 g HgSO4 in 40 mL of 2N H2SO4 was added 5.0 g (31 mmol) of the 3,4-epoxy-3-(4'-fluorophenyl)-1-butyne in 40 mL of absolute ethanol, dropwise. The reaction mixture was refluxed for 0.25 hour and cooled to 23° C. After addition to 50 mL of H2O, the aqueous phase was extracted twice with hexanes. The hexane layers were combined, dried (MgSO4) and concentrated under reduced pressure. Sublimation (90° C. at 0.2 mmHg) of the residue yielded 2.9 g (58%) of the 2-(4'-fluorophenyl)furan as a solid (m.p. 84°-86° C.) homogeneous by spectroscopic criteria; IR (film) 1571, 1505, 1223, 1152, 785 cm-1 ; 1HNMR (80 MHz, CDCl3) 7.5-7.0 (m, 6H), 6.65 (m, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 0.25 hour
  2. extractionthe aqueous phase was extracted twice with hexanes
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d6cc4faf708a447f9a08b54b7def2ecd
Source dataset
uspto-grants-1988_12
Patent number
US04792614

Reaction notes

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