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Hydrochloric Acid → 2-[(3,4-Dimethoxyphenyl)thio]-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxylic acid

HRID 1107129
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HRID 1107129 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][C:12]2[C:16](=[CH:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14][C:13]=2[C:26]([O:28]C)=[O:27])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[Na+].Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][C:12]2[C:16](=[CH:17][CH2:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:15][CH2:14][C:13]=2[C:26]([OH:28])=[O:27])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69907819Methyl 2-[(3,4-dimethoxyphenyl)thio]-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxylate

생성물 1

HCID 699076212-[(3,4-Dimethoxyphenyl)thio]-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxylic acid수율 85%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of methyl 2-[(3,4-dimethoxyphenyl)thio]-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxylate (0.5 g, 1.2 mmol) and 10% sodium hydroxide (5 mL) in ethanol (10 mL) is heated under reflux for 4 hours. The mixture is cooled and is poured into aqueous HCl. The mixture is extracted with ether. The organic layer is washed with water and is dried over MgSO4. The solvent is removed in vacuo to provide 2-[(3,4-dimethoxyphenyl)thio]-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxylic acid (0.4 g, 85%): m.p. 146-8° C. Anal. (C23H26O4S) C,H,N: 1H-NMR (300 MHz, CDCl3) δ (TMS) 1.10-1.70 (m, 5H), 1.83-2.02 (m, 1H), 2.32-2.41 (t, 2H), 2.60-2.72 (m, 3H), 3.84 (s, 3H), 3.90 (s, 3H), 6.69-6.75 (d, 1H), 6.94-7.00 (m, 2H), 7.00-7.10 (d, 2H), 7.18-7.32 (m, 3H); MS (EI) m/e 398 (M+).

후처리

  1. temperatureis heated
  2. temperatureunder reflux for 4 hours
  3. temperatureThe mixture is cooled
  4. extractionThe mixture is extracted with ether
  5. washThe organic layer is washed with water
  6. dry with materialis dried over MgSO4
  7. customThe solvent is removed in vacuo

출처 및 근거

ORD 기록
ord-cc3cbc8ba8f74c9e894b0ca18b16176f
출처 데이터셋
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06057369

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