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

HRID 62000ノート

反応式

HRID 62000 の反応式
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]

参加物

5

反応物 3

HCID 8000Boron trifluoride etherateHCID 64250582-(Trifluoromethyl)nicotinamideHCID 67037149HCID 67037149、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-c249d2293de14c54a553af49a4fe494b
出典データセット
uspto-grants-2016_09
特許番号
US09446012B2

反応ノート

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