Boron trifluoride etherate → HCID 67036906、化合物

HRID 1920073ノート

反応式

HRID 1920073 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.[C:21]([C:24]1[C:25]([C:31]([F:34])([F:33])[F:32])=[N+:26]([O-:30])[CH:27]=[CH:28][CH:29]=1)(=[O:23])[NH2:22].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:22]=[C:21]([C:24]3[C:25]([C:31]([F:32])([F:34])[F:33])=[N+:26]([O-:30])[CH:27]=[CH:28][CH:29]=3)[O:23][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 670370223-Carbamoyl-2-(trifluoromethyl)pyridine 1-oxideHCID 67037149HCID 67037149、化合物

生成物 1

HCID 67036906HCID 67036906、化合物

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 3-carbamoyl-2-(trifluoromethyl)pyridine 1-oxide (3.40 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 3-(4-(3,4-dimethoxy-5-nitrophenyl)oxazol-2-yl)-2-(trifluoromethyl)pyridine 1-oxide was obtained by column chromatography over silica gel (petroleum ether/ethylacetate 2:1) as a pale yellow solid, 2.58 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-b95b6dca456141cc9da1bb617cf0892c
出典データセット
uspto-grants-2012_05
特許番号
US08168793B2

反応ノート

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