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

HRID 1107129
ノート
印刷プレビュー

反応式

HRID 1107129 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-cc3cbc8ba8f74c9e894b0ca18b16176f
出典データセット
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06057369

反応ノート

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