Benzyl Alcohol → 1-(4-Benzyloxy-3-trifluoromethyl-phenyl)-ethanone

HRID 2167836노트

반응식

HRID 2167836 반응식
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].F[C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:24])[CH3:23])=[CH:18][C:17]=1[C:25]([F:28])([F:27])[F:26]>C1COCC1>[CH2:1]([O:8][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:24])[CH3:23])=[CH:18][C:17]=1[C:25]([F:26])([F:27])[F:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 244Benzyl AlcoholHCID 6056784'-Fluoro-3'-(trifluoromethyl)acetophenoneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 670324791-(4-Benzyloxy-3-trifluoromethyl-phenyl)-ethanone수율 72.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of benzyl alcohol (10.9 mL; 104.98 mmol) and KOtBu (12.96 g; 115.5 mmol) in THF (500 mL) was heated under reflux for 10 minutes. Subsequently, 4′-fluoro-3′-(trifluoromethyl)acetophenone (21.64 g; 105 mmol) was added and the mixture heated under reflux for another 2 hours. After cooling to RT, the mixture was partitioned between EtOAc and a 5% aqueous NaHCO3 solution. The organic layer was separated, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O:hexanes 1:2.5) to afford 1-(4-Benzyloxy-3-trifluoromethyl-phenyl)-ethanone (22.37 g).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 10 minutes
  3. temperaturethe mixture heated
  4. temperatureunder reflux for another 2 hours
  5. customthe mixture was partitioned between EtOAc
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by column chromatography (SiO2, Et2O:hexanes 1:2.5)

출처 및 근거

ORD 기록
ord-7a375697b36a46c98e020a6e5c44723d
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045441B2

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