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

HRID 1161133Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1161133
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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9e0c0c18037747bea4ce55ba9e4e58b6
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816523B2

Notizen zur Reaktion

Wird geladen…