Potassium Hydroxide → 1-(3,4-Methylenedioxyphenyl)-3-phenylindane-2-carboxylic acid

HRID 650760ノート

反応式

HRID 650760 の反応式
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:12]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:11]3[C:25]([O-:27])=[O:26])=[CH:4][C:3]=2[O:2]1.[OH-].[K+]>CCO.C1COCC1>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:12]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:11]3[C:25]([OH:27])=[O:26])=[CH:4][C:3]=2[O:2]1

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 217147891-(3,4-Methylenedioxyphenyl)-3-phenylindane-2-carboxylate

生成物 1

HCID 217147901-(3,4-Methylenedioxyphenyl)-3-phenylindane-2-carboxylic acid

試薬・触媒・溶媒 2

HCID 702Ethanol触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of ethyl (1RS, 2SR, 3SR)-1-(3,4-methylenedioxyphenyl)-3-phenylindane-2-carboxylate (650 mg, 1.68 mmol) in EtOH containing a few drops of THF was added 6M KOH (1.68 ml, 10.1 mmol). The resulting mixture was allowed to stir at room temperature overnight, then was concentrated under reduced pressure. The residue was partitioned between H2O and Et2O. The aqueous phase was acidified with 3M HCl and extracted several times with EtOAc. The combined EtOAc extracts were washed successively with H2O and saturated aqueous NaCl and dried (MgSO4). The solvent was removed in vacuo to afford an oil, which was crystallized from EtOAc/hexanes. The title compound was obtained as a solid (305 mg, 51%); m.p. 186-187° C.

後処理

  1. concentrationwas concentrated under reduced pressure
  2. customThe residue was partitioned between H2O and Et2O
  3. extractionextracted several times with EtOAc
  4. washThe combined EtOAc extracts were washed successively with H2O and saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customto afford an oil, which
  8. customwas crystallized from EtOAc/hexanes

出典と根拠

ORDレコード
ord-68a5652a85b4412d8fc52aa075668373
出典データセット
uspto-grants-2001_08
特許番号
US06274737B1

反応ノート

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