Water → 2-Methyl-4-(4'-fluorophenyl)furan

HRID 414642Notes

Reaction equation

[O:1]1[CH2:6][C:2]1([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)[CH2:3][C:4]#[CH:5].O>OS(O)(=O)=O.C(O)C>[CH3:5][C:4]1[O:1][CH:6]=[C:2]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[CH:3]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of 0.46 g (1.5 mmol) of mercuric sulfate in 28 mL of 2N H2SO4 at 0° C. was added 4.0 g (22 mmol) of 4,5-epoxy-4-(4'-fluorophenyl)-1-pentyne in 20 mL of ethanol over a 0.5 hour period. The mixture was warmed to 23° C. for 0.25 hour and refluxed for 0.25 hour. After cooling, the mixture was poured into 50 mL of H2O and extracted three times with hexanes. The organic layer was dried (MgSO4), concentrated under reduced pressure, and the solid sublimated (97°-105° C. at 15 mmHg) to yield 2.2 g (55%) of 2-methyl-4-(4'-fluorophenyl)furan as a solid (m.p. 95°-97° C.), homogeneous by spectroscopic criteria; IR (KBr) 1548, 1495, 1240 cm-1 ; 1HNMR (300 MHz, CDCl3) δ 7.55 (s, 1H), 7.43 (m, 2H), 7.07 (t, 2H, J=9 Hz), 6.27 (s, 1H), 2.33 (s, 3H).

Workup

temperaturerefluxed for 0.25 hour
temperatureAfter cooling
extractionextracted three times with hexanes
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-523c321604f740e4872bc82c6bc00850
Source dataset: uspto-grants-1988_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04792614

Reaction notes

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