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

HRID 428388

반응식

HRID 428388 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-11c5427b9de541789feec08b0bde27a8
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313295B1

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