Boron trifluoride etherate → 4-(3,4-Dimethoxy-5-nitrophenyl)-2-(2-(trifluoromethyl)pyridin-3-yl)oxazole

HRID 62000노트

반응식

HRID 62000 반응식
C(O[CH2:5][C:6]([C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([O:17][CH3:18])=[C:10]([O:19][CH3:20])[CH:9]=1)=O)(=O)C.[F:21][C:22]([F:33])([F:32])[C:23]1[N:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25]([NH2:27])=[O:26].B(F)(F)F.CCOCC>C1(C)C(C)=CC=CC=1>[CH3:20][O:19][C:10]1[CH:9]=[C:8]([C:6]2[N:27]=[C:25]([C:24]3[C:23]([C:22]([F:32])([F:21])[F:33])=[N:31][CH:30]=[CH:29][CH:28]=3)[O:26][CH:5]=2)[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]=1[O:17][CH3:18]

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 64250582-(Trifluoromethyl)nicotinamideHCID 67037149HCID 67037149, 화합물

생성물 1

HCID 687013284-(3,4-Dimethoxy-5-nitrophenyl)-2-(2-(trifluoromethyl)pyridin-3-yl)oxazole

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

To a solution of 2-(3,4-dimethoxy-5-nitrophenyl)-2-oxoethyl acetate (4.24 g, 15 mmol) in xylene (30 mL) were added 2-(trifluoromethyl)nicotinamide (3.135 g, 16.5 mmol) and boron trifluoride etherate (0.18 mL, 15 mmol). The resulting yellow solution was heated to reflux for 18 hours and then cooled to room temperature. After evaporation of the solvent, the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was separated, washed with brine and the dried over anhydrous magnesium sulphate, filtered and evaporated. The pure 4-(3,4-dimethoxy-5-nitrophenyl)-2-(2-(trifluoromethyl)pyridin-3-yl)oxazole was obtained by column chromatography over silica gel (petroleum ether/ethylacetate 2:1) as a pale yellow solid, 2.488 g (42%).

후처리

  1. temperatureThe resulting yellow solution was heated
  2. temperatureto reflux for 18 hours
  3. customAfter evaporation of the solvent
  4. customthe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  5. customThe organic phase was separated
  6. washwashed with brine
  7. dry with materialthe dried over anhydrous magnesium sulphate
  8. filtrationfiltered
  9. customevaporated

출처 및 근거

ORD 기록
ord-c249d2293de14c54a553af49a4fe494b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09446012B2

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