Potassium Carbonate → 4-(3-Isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-benzaldehyde

HRID 1007477노트

반응식

HRID 1007477 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].[F:20][C:21]([F:36])([F:35])[C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([C:31]([F:34])([F:33])[F:32])[C:29]=1Cl)[CH:25]=[O:26].[Cl-].[NH4+]>CS(C)=O.C(OCC)(=O)C>[CH:11]([C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([O:1][C:29]3[C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][C:22]=3[C:21]([F:20])([F:35])[F:36])[CH:3]=2)[NH:7][CH:6]=1)([CH3:13])[CH3:12]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 226694913-isopropyl-1H-indol-5-olHCID 226696144-Chloro-3,5-bis(trifluoromethyl)benzaldehyde

생성물 1

HCID 226698054-(3-Isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-benzaldehyde

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

12.8 g (70.27 mmol) of 5-hydroxy-3-isopropyl-indole are dissolved in 275.8 ml of DMSO, 10.68 g (77.3 mmol) of potassium carbonate are introduced in solid form, the mixture is stirred for 10 minutes at room temperature and afterwards 19.43 g (70.27 mmol) of 3,5-bistrifluoromethyl-4-chlorobenzaldehyde are introduced in portions. After stirring at 50° C. for 3 hours the batch is poured onto a mixture of 400 ml of ethyl acetate and 250 ml of saturated ammonium chloride solution. After phase separation, the aqueous phase is extracted again with ethyl acetate, and the combined organic phases are washed twice with sodium chloride solution and dried over sodium sulphate. After removing the drying agent and distilling off the solvent the crude product is chromatographed on silica gel 60 (Merck 0.040-0.063 mm) using toluene.

후처리

  1. stirringAfter stirring at 50° C. for 3 hours the batch
  2. customAfter phase separation
  3. extractionthe aqueous phase is extracted again with ethyl acetate
  4. washthe combined organic phases are washed twice with sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. customAfter removing the drying agent
  7. distillationdistilling off the solvent the crude product
  8. customis chromatographed on silica gel 60 (Merck 0.040-0.063 mm)

출처 및 근거

ORD 기록
ord-40cd6c5262594729809ad3a35539aae5
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06794406B2

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