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

HRID 1451528ノート

反応式

HRID 1451528 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-50847f5d1f97465fabf729316bda380b
出典データセット
uspto-grants-1997_02
特許番号
US05604253

反応ノート

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