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

HRID 399219노트

반응식

HRID 399219 반응식
[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

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-5eec84059cab46468c60bf78b26efb1b
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05817693

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