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

HRID 414642노트

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HRID 414642 반응식
[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

참가 물질

5

반응물 2

HCID 962WaterHCID 144246744,5-Epoxy-4-(4'-fluorophenyl)-1-pentyne

생성물 1

HCID 144246752-Methyl-4-(4'-fluorophenyl)furan수율 56.8%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 1118Sulfuric Acid용매

반응 조건

온도
23 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-523c321604f740e4872bc82c6bc00850
출처 데이터셋
uspto-grants-1988_12
특허 번호
US04792614

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