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

HRID 9667

반응식

HRID 9667 반응식
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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-450d571946b54fa997b752c94963e482
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091237B2

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