Ethyl Acetate → HCID 86685848, 화합물

HRID 1629759노트

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HRID 1629759 반응식
[F:1][C:2]([F:20])([F:19])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[CH:7][CH:6]=1)[OH:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>C(Cl)Cl>[F:1][C:2]([F:19])([F:20])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[CH:7][CH:6]=1)=[O:4]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 159087TriacetoxyperiodinaneHCID 866858472,2,2-Trifluoro-1-(4-(4,4,4-trifluorobutoxy)phenyl)ethanol

생성물 1

HCID 86685848HCID 86685848, 화합물수율 76%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of Intermediate 2B (115 mmol) in anhydrous CH2Cl2 (320 mL) was added Dess-Martin periodinane (50.2 g, 118 mmol) portionwise at 0° C. The reaction was stirred at 0° C. for 0.5 h then at rt for 3 h. To the reaction was added 100 mL of sat'd aq Na2CO3 and 250 mL of EtOAc. The reaction was stirred for another 2 h. The insoluble material was removed by filtration. The layers were separated. The organic layer was washed with sat'd aq Na2CO3. Additional solids that formed upon standing overnight were removed. The organic solution was washed with sat'd aq NaCl, dried over anhydrous MgSO4, filtered and concentrated to provide a dark brown liquid, which was purified by silica gel chromatography (220 g silica gel, elute with EtOAc in hexanes to provide Intermediate 2C (26 g, 76%) as a colorless oil.

후처리

  1. waitat rt for 3 h
  2. stirringThe reaction was stirred for another 2 h
  3. customThe insoluble material was removed by filtration
  4. customThe layers were separated
  5. washThe organic layer was washed with sat'd aq Na2CO3
  6. customAdditional solids that formed
  7. waitupon standing overnight
  8. customwere removed
  9. washThe organic solution was washed with sat'd aq NaCl
  10. dry with materialdried over anhydrous MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customto provide a dark brown liquid, which
  14. customwas purified by silica gel chromatography (220 g silica gel
  15. washelute with EtOAc in hexanes

출처 및 근거

ORD 기록
ord-fdaa27e430c14a5fad0e1a18a3d9d11c
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791091B2

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