Ethyl (RS)-1,3-Di-(3,4-methylenedioxyphenyl)indene-2-carboxylate → ethyl(1RS,3RS)-1,3-di-(3,4-methylenedioxyphenyl)indane-2-carboxylate

HRID 399219ノート

反応式

HRID 399219 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)[C:12]([C:19]4[CH:24]=[CH:23][C:22]5[O:25][CH2:26][O:27][C:21]=5[CH:20]=4)=[C:11]3[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:4][C:3]=2[O:2]1>CO>[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][C:22]5[O:25][CH2:26][O:27][C:21]=5[CH:20]=4)[CH:11]3[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:4][C:3]=2[O:2]1

参加物

3

反応物 1

HCID 21714780Ethyl (RS)-1,3-Di-(3,4-methylenedioxyphenyl)indene-2-carboxylate

生成物 1

HCID 18969665ethyl(1RS,3RS)-1,3-di-(3,4-methylenedioxyphenyl)indane-2-carboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Ethyl(RS)-1,3-di-(3,4-Methylenedioxyphenyl)indene-2-carboxylate (163 mg, 0.38 mmol) was placed in MeOH (0.05 ml), and to this was added SmI2 (10 ml of 0.1M solution in THF, 1.0 mmol). The resulting mixture was stirred under an argon atmosphere overnight, at which time thin layer chromatographic analysis indicated that the reaction was incomplete. Additional SmI2 (5 ml of 0.1M solution in THF, 0.5 mmol) was added, and stirring was continued for 2 h. The reaction mixture was partitioned between Et2O and 5% aqueous Na2S2O3. The organic extract was washed with saturated aqueous NaCl and dried (MgSO4). The solvent was removed under reduced pressure, and the residue was purified by flash chromatography, eluting with 10% EtOAc/hexanes to afford the title compound as a colorless, glassy solid (120 mg, 75%).

後処理

  1. stirringstirring
  2. waitwas continued for 2 h
  3. customThe reaction mixture was partitioned between Et2O and 5% aqueous Na2S2O3
  4. extractionThe organic extract
  5. washwas washed with saturated aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by flash chromatography
  9. washeluting with 10% EtOAc/hexanes

出典と根拠

ORDレコード
ord-5eec84059cab46468c60bf78b26efb1b
出典データセット
uspto-grants-1998_10
特許番号
US05817693

反応ノート

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