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Acetic Acid → 4-(2-Carboxy-2-ethoxy-ethyl)-benzoic acid 4-methanesulfonyloxy-benzyl ester

HRID 709505
ノート
印刷プレビュー

反応式

HRID 709505 の反応式
[CH3:1][S:2]([O:5][C:6]1[CH:34]=[CH:33][C:9]([CH2:10][O:11][C:12](=[O:32])[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([O:29][CH2:30][CH3:31])[C:21]([O:23]CC(Cl)(Cl)Cl)=[O:22])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].C(O)(=O)C>C(Cl)Cl.[Zn]>[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][O:11][C:12](=[O:32])[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([C:21]([OH:23])=[O:22])[O:29][CH2:30][CH3:31])=[CH:15][CH:14]=2)=[CH:33][CH:34]=1)(=[O:4])=[O:3]
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 2

HCID 176Acetic AcidHCID 866503074-[2-Ethoxy-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl]-benzoic acid 4-methane sulfonyloxy-benzyl ester

生成物 1

HCID 866503144-(2-Carboxy-2-ethoxy-ethyl)-benzoic acid 4-methanesulfonyloxy-benzyl ester

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-[2-ethoxy-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl]-benzoic acid 4-methane sulfonyloxy-benzyl ester (0.02 g, 0.036 mmol) in dry DCM (2 mL) was first added zinc dust (0.047 g, 0.722 mmol), then acetic acid (1.08 mL, 18.06 mmol) at 0° C. The resulting inhomogeneous mixture was stirred for 17 h without removing the ice bath. The zinc was filtered off and washed with DCM and MeOH and the remaining filtrates were combined and evaporated under reduced pressure. The crude product was purified by column chromatography using DCM/MeOH (92:8) as the eluent. The title compound was obtained as an oil (0.005 g, 36%). 1H NMR (400 MHz, CDCl3): δ 7.91-7.93 (d, 2H), 7.42-7.44 (d, 2H, 7.19-7.24 (m, 4H), 5.27 (s, 2H), 4.03 (m, 1H), 3.52 (m, 1H), 3.37 (m, 1H), 2.99-3.14 (m, 2H), 3.08 (s, 3H), 2.63 (t, 3H). Mass Spectrum: M−H+ 421.23.

後処理

  1. customat 0° C
  2. customwithout removing the ice bath
  3. filtrationThe zinc was filtered off
  4. washwashed with DCM and MeOH
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-fbf367028dd74c4283ba7e65995d5157
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181181B2

反応ノート

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