Sodium Hydroxide → 3-[1-(p-Bromobenzyl)-5-methoxy-2-methylindol-3-yl]-4,4,4-trifluorobutanoic acid

HRID 1451528노트

반응식

HRID 1451528 반응식
[Br:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH:18]([C:25]([F:28])([F:27])[F:26])[CH2:19][C:20]([O:22]CC)=[O:21])=[C:8]2[CH3:29])=[CH:4][CH:3]=1.[OH-].[Na+].CCOCC.CCCCCC>CCO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH:18]([C:25]([F:28])([F:26])[F:27])[CH2:19][C:20]([OH:22])=[O:21])=[C:8]2[CH3:29])=[CH:30][CH:31]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 19974932Ethyl 3-[1-(p-bromobenzyl)-5-methoxy-2-methylindol-3-yl]-4,4,4-trifluorobutanoatHCID 21584099Diethylether hexane

생성물 1

HCID 221489393-[1-(p-Bromobenzyl)-5-methoxy-2-methylindol-3-yl]-4,4,4-trifluorobutanoic acid수율 92.5%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a mixture of the ester from Step 4 (4.6 g, 9.2 mmol) in 45 mL of EtOH was added 10N NaOH (2.3 mL, 23 mmol) and the mixture was heated to reflux for 2 h. The mixture was cooled and concentrated and the residue was partitioned between ether and 1M HCl. The organic layer was dried over MgSO4 and evaporated to give a white solid. This material was swished with 10% ether/hexane to give 4.0 g of the title compound.

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 h
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. customthe residue was partitioned between ether and 1M HCl
  6. dry with materialThe organic layer was dried over MgSO4
  7. customevaporated
  8. customto give a white solid

출처 및 근거

ORD 기록
ord-50847f5d1f97465fabf729316bda380b
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05604253

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