Ethyl Acetate → 3-[4-(4-Acetyl-3-hydroxy-2-iodo-phenoxymethyl)-benzyl]-benzoic acid methyl ester

HRID 1161133ノート

反応式

HRID 1161133 の反応式
C(=O)([O-])[O-].[K+].[K+].[C:7]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([I:17])[C:11]=1[OH:18])(=[O:9])[CH3:8].[CH3:19][O:20][C:21](=[O:37])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([CH2:35]I)=[CH:31][CH:30]=2)[CH:23]=1.C(OCC)(=O)C>CC(C)=O.ClCCl>[CH3:19][O:20][C:21](=[O:37])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][C:29]2[CH:30]=[CH:31][C:32]([CH2:35][O:16][C:13]3[CH:14]=[CH:15][C:10]([C:7](=[O:9])[CH3:8])=[C:11]([OH:18])[C:12]=3[I:17])=[CH:33][CH:34]=2)[CH:23]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 132755071-(2,4-Dihydroxy-3-iodophenyl)ethan-1-oneHCID 574383993-(4-Iodomethyl-benzyl)-benzoic acid methyl ester

生成物 1

HCID 666995233-[4-(4-Acetyl-3-hydroxy-2-iodo-phenoxymethyl)-benzyl]-benzoic acid methyl ester収率 61%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

Potassium carbonate (675 mg, 4.88 mmol) is added to a solution of 4-acetyl-3-hydroxy-2-iodo-phenol (925 mg, 3.33 mmol) and 3-(4-iodomethyl-benzyl)-benzoic acid methyl ester (1.21 g, 3.30 mmol) in acetone (65 mL). The resulting suspension is heated at 50° C. for 16 hours. The reaction mixture is cooled to room temperature and concentrated in vacuo. The residue is taken up in dichloromethane, washed with 1N hydrochloric acid, brine, dried over magnesium sulfate, filtered and concentrated to give a yellow solid. This solid is dissolved in dichloromethane and a white precipitate forms upon addition of ethyl acetate. The white solid is filtered off and the mother liquor is purified by flash chromatography, eluting with 20% ethyl acetate in hexanes. The precipitate and chromatographed materials are combined to give 1.04 g of the title compound as a pale yellow solid: MS (m/z) 517 (M+1), 515 (M−1); 1H NMR δ (CDCl3); 13.58 (s, 1H), 7.93 (m, 2H), 7.74 (d, J=9.0 Hz, 1H), 7.45-7.38 (m, 4H), 7.25 (d, J=8.0 Hz, 2H), 6.50 (d, J=9.0 Hz, 1H), 5.27 (s, 2H), 4.07 (s, 2H), 3.94 (s, 3H), 2.63 (s, 3H).

後処理

  1. temperatureThe reaction mixture is cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. washwashed with 1N hydrochloric acid, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a yellow solid
  8. filtrationThe white solid is filtered off
  9. customthe mother liquor is purified by flash chromatography
  10. washeluting with 20% ethyl acetate in hexanes
  11. customThe precipitate and chromatographed materials

出典と根拠

ORDレコード
ord-9e0c0c18037747bea4ce55ba9e4e58b6
出典データセット
uspto-grants-2010_10
特許番号
US07816523B2

反応ノート

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