Diethyl Ether → 2-Cyclopropoxy-5-(trifluoromethoxy)benzaldehyde

HRID 323759

반응식

HRID 323759 반응식
[CH:1]1([O:4][C:5]2[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][C:6]=2I)[CH2:3][CH2:2]1.C([SnH](CCCC)CCCC)CCC.[C]=O.C[CH2:33][O:34]CC>C1(C)C=CC=CC=1.[F-].[K+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:1]1([O:4][C:5]2[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][C:6]=2[CH:33]=[O:34])[CH2:3][CH2:2]1

참가 물질

8

반응물 4

HCID 3283Diethyl EtherHCID 5948TributylstannaneHCID 117596921-(Cyclopropyloxy)-2-iodo-4-(trifluoromethoxy)benzeneHCID 178418416HCID 178418416, 화합물

생성물 1

HCID 215840762-Cyclopropoxy-5-(trifluoromethoxy)benzaldehyde

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매2회HCID 522689Potassium Fluoride용매

반응 조건

온도
50 °C

실험 절차

A solution of 2-cyclopropoxy-5-(trifluoromethoxy)iodobenzene (Description 8, 0.344 g, 1 mmol) in toluene (2.5 mL) was degassed with bubbling nitrogen for 10 min. Tetrakis(triphenylphosphine)palladium (0) (15 mg) was added, the mixture was degassed with bubbling nitrogen for a further 5 min., then carbon monoxide was bubbled through the mixture for 10 min. The mixture was warmed to 50° C. and a solution of tributyl tin hydride (0.3 mL, 1.1 mmol) in toluene (5 mL) was added at a rate of 2 mL/h. via a syringe pump, maintaining carbon monoxide bubbling throughout. The mixture was cooled, diluted with ether (20 mL) and aqueous potassium fluoride solution (50%) was added. The mixture was stirred at room temperature overnight, filtered and the layers were separated. The organic layer was dried (MgSO4), and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/Et2O (80:20), to give the title compound as a colourless oil. 1H NMR (360 MHz, CDCl3) δ0.86 (4H, m), 3.82-3.9 (1H, m), 7.42 (2H, m), 7.62 (1H, d, J 2.5 Hz), and 10.36 (1H, s).

후처리

  1. customthe mixture was degassed with bubbling nitrogen for a further 5 min.
  2. customcarbon monoxide was bubbled through the mixture for 10 min
  3. temperatureThe mixture was cooled
  4. additionwas added
  5. filtrationfiltered
  6. customthe layers were separated
  7. dry with materialThe organic layer was dried (MgSO4)
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by flash column chromatography on silica gel
  10. washeluting with hexane/Et2O (80:20)

출처 및 근거

ORD 기록
ord-2871bc268c9646019041de0d623366b1
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06214846B1

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