Potassium Carbonate → 4-Ethyl-5-(2-fluoro-4-(trifluoromethyl)phenyl)oxazole

HRID 1672579ノート

反応式

HRID 1672579 の反応式
[N+:1]([CH:3](S(C1C=CC(C)=CC=1)(=O)=O)[CH2:4][CH3:5])#[C-:2].[F:16][C:17]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:18]=1[CH:19]=[O:20].C([O-])([O-])=O.[K+].[K+]>CO>[CH2:4]([C:3]1[N:1]=[CH:2][O:20][C:19]=1[C:18]1[CH:21]=[CH:22][C:23]([C:25]([F:26])([F:27])[F:28])=[CH:24][C:17]=1[F:16])[CH3:5]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 5229292-Fluoro-4-(trifluoromethyl)benzaldehydeHCID 204671891-Ethyl-1-tosylmethyl isocyanide

生成物 1

HCID 666966994-Ethyl-5-(2-fluoro-4-(trifluoromethyl)phenyl)oxazole収率 50%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 1-(1-isocyanopropylsulfonyl)-4-methylbenzene (1.55 g, 6.94 mmol), 2-fluoro-4-(trifluoromethyl)benzaldehyde (0.95 mL, 6.9 mmol), and K2CO3 (1.15 g, 8.33 mmol) in MeOH (35 mL) was heated at reflux overnight. The reaction was cooled to ambient temperature and the volatiles evaporated at reduced pressure. The residue was diluted with water and the product extracted with EtOAc. The combined organic extract was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was chromatographed on silica gel (Analogix® 40×150 column, 10%-70% EtOAc/hexanes) to yield 0.89 g (50%) of the title compound. 1H NMR (300 MHz, CDCl3) δ 7.95 (s, 1H), 7.67-7.60 (m, 1H), 7.53-7.48 (m, 1H), 7.47-7.42 (m, 1H), 2.67 (qd, J=7.5, 1.6, 2H), 1.29 (t, J=7.5, 3H). MS (DCI+) m/z 260 (M+H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customthe volatiles evaporated at reduced pressure
  4. additionThe residue was diluted with water
  5. extractionthe product extracted with EtOAc
  6. extractionThe combined organic extract
  7. washwas washed with water and brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude product was chromatographed on silica gel (Analogix® 40×150 column, 10%-70% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-ad43de420ecb481f83218d29b909447f
出典データセット
uspto-grants-2011_08
特許番号
US07998993B2

反応ノート

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