Water → 3-[3-(4-Acetyl-3-hydroxy-2-propyl-phenylsulfanylmethyl)-benzyl]-benzoic acid methyl ester

HRID 1818467Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1818467
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([SH:11])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].[CH3:15][O:16][C:17](=[O:33])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31]I)[CH:26]=2)[CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CC(=O)CC>[CH3:15][O:16][C:17](=[O:33])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][S:11][C:6]3[CH:5]=[CH:4][C:3]([C:12](=[O:14])[CH3:13])=[C:2]([OH:1])[C:7]=3[CH2:8][CH2:9][CH3:10])[CH:26]=2)[CH:19]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 132955181-(2-Hydroxy-3-propyl-4-sulfanylphenyl)ethan-1-oneHCID 574383053-(3-Iodomethyl-benzyl)-benzoic acid methyl ester

Produkt 1

HCID 666995593-[3-(4-Acetyl-3-hydroxy-2-propyl-phenylsulfanylmethyl)-benzyl]-benzoic acid methyl esterAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

Stir a mixture of 1-(2-Hydroxy-4-mercapto-3-propyl-phenyl)-ethanone (132 mg, 0.63 mmol), 3-(3-Iodomethyl-benzyl)-benzoic acid methyl ester (230 mg, 0.63 mmol), and cesium carbonate (410 mg, 1.26 mmol) in 2-butanone (6 ml) at room temperature under argon for 20 hours. Pour the mixture into water (60 ml) and extract with ethyl acetate (2×30 ml). Combine the organic extracts and wash with water, brine, then dry over sodium sulfate, filter and concentrate. Purify the crude product via silica chromatography eluting with 1:4 ethyl acetate:hexanes to give the title compound (240 mg, 85%). MS (m/z) 447 (M−H).

Aufarbeitung

  1. extractionextract with ethyl acetate (2×30 ml)
  2. washCombine the organic extracts and wash with water, brine
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the crude product via silica chromatography
  7. washeluting with 1:4 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-e2dc3aa151884fb5a30ea580ab73b6af
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598423B2

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