Triethylamine → 6-Fluoro-3-methyl-1,2-benzoxazole

HRID 428388

反応式

HRID 428388 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[C:4]([OH:11])[CH:3]=1.C(N1C=CN=C1)([N:14]1C=CN=C1)=O.C(N(CC)CC)C>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]([CH3:9])=[N:14][O:11][C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 27373264'-Fluoro-2'-hydroxyacetophenone

生成物 1

HCID 219784096-Fluoro-3-methyl-1,2-benzoxazole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A mixture of 4′-fluoro-2′-hydroxyacetophenone, oxime (47.0 g, 0.278 mol) in tetrahydrofuran is heated to just under reflux, treated with a solution of 1,1′-carbonyldiimidazole (55.0 g, 0.340 mol) and triethylamine (39.0 g, 0.390 mol) in tetrahydrofuran, refluxed for one hour, cooled, concentrated in vacuo, and poured into an ice-water mixture. The resultant aqueous mixture is extracted with ether. The organic extracts are combined, washed sequentially with saturated ammonium chloride solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain an oil. Column chromatography of the oil using silica gel and a methylene chloride/hexanes solution (1:1) gives the title product as a yellow oil which is identified by 1H NMR spectral analysis.

後処理

  1. temperatureis heated to just
  2. temperatureunder reflux
  3. temperaturerefluxed for one hour
  4. temperaturecooled
  5. concentrationconcentrated in vacuo
  6. additionpoured into an ice-water mixture
  7. extractionThe resultant aqueous mixture is extracted with ether
  8. washwashed sequentially with saturated ammonium chloride solution and brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customto obtain an oil

出典と根拠

ORDレコード
ord-11c5427b9de541789feec08b0bde27a8
出典データセット
uspto-grants-2001_11
特許番号
US06313295B1

関連ノート

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