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

HRID 414642ノート

反応式

HRID 414642 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 144246752-Methyl-4-(4'-fluorophenyl)furan収率 56.8%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 1118Sulfuric Acid溶媒

反応条件

温度
23 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-523c321604f740e4872bc82c6bc00850
出典データセット
uspto-grants-1988_12
特許番号
US04792614

反応ノート

読み込み中…