Methanesulfonic Acid → 2-(4-Methoxy-3-methylphenyl)-1-{3-methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}ethanone

HRID 9667

反応式

HRID 9667 の反応式
CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([OH:31])=O)=[CH:24][C:23]=1[CH3:32].[CH3:33][C:34]1[CH:35]=[C:36]([C:39]2[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:41][CH:40]=2)[S:37][CH:38]=1.C([O-])(O)=O.[Na+]>O>[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([C:38]2[S:37][C:36]([C:39]3[CH:40]=[CH:41][C:42]([C:45]([F:46])([F:48])[F:47])=[CH:43][CH:44]=3)=[CH:35][C:34]=2[CH3:33])=[O:31])=[CH:24][C:23]=1[CH3:32]

参加物

7

反応物 5

HCID 6395Methanesulfonic AcidHCID 14812Phosphorus oxide (P4O10)HCID 1382764-Methoxy-3-methylphenylacetic acidHCID 516892Sodium BicarbonateHCID 21986373Thiophene, 4-methyl-2-[4-(trifluoromethyl)phenyl]-2 回

生成物 1

HCID 219863702-(4-Methoxy-3-methylphenyl)-1-{3-methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}ethanone

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

To methanesulfonic acid (8 ml) in a flask under N2 was added P2O5 (0.56 g), the resulting suspension was heated to 60° C. until a clear solution formed. The mixture was cooled to room temperature prior to addition of 4-methoxy-3-methyl-phenylacetic acid (0.3549) and 4-methyl-2-[4-(trifluoromethyl)phenyl]thiophene (intermediate 102, 0.4 g). The mixture was then heated to 60° C. for 90 minutes. The reaction mixture was cooled to room temperature and then poured into iced water. The suspension was made basic by cautious addition of NaHCO3 and the products extracted into ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and evaporated to yield a brown oil. Purification by flash column chromatography eluting with 5% EtOAc/cyclohexane yielded the title compound as a brown gum.

後処理

  1. customformed
  2. temperatureThe mixture was cooled to room temperature
  3. temperatureThe mixture was then heated to 60° C. for 90 minutes
  4. temperatureThe reaction mixture was cooled to room temperature
  5. extractionthe products extracted into ethyl acetate
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto yield a brown oil
  10. customPurification by flash column chromatography
  11. washeluting with 5% EtOAc/cyclohexane

出典と根拠

ORDレコード
ord-450d571946b54fa997b752c94963e482
出典データセット
uspto-grants-2006_08
特許番号
US07091237B2

関連ノート

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