4-Methoxymandelic acid → 2-Trimethylsilylethyl 4-methoxymandelate

HRID 1534093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1534093
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]([OH:11])[C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1.[CH3:14][Si:15]([CH3:29])([CH3:28])[CH2:16][CH2:17]N=C(O)N(C(C)C)C(C)C>O1CCOCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:7]([OH:11])[C:8]([O:10][CH2:17][CH2:16][Si:15]([CH3:29])([CH3:28])[CH3:14])=[O:9])=[CH:12][CH:13]=1

Komponenten

5

Edukt 2

HCID 1120564-Methoxymandelic acidHCID 178457954HCID 178457954, Verbindung

Produkt 1

HCID 137057282-Trimethylsilylethyl 4-methoxymandelateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 4-methoxymandelic acid (2.00 g, 10.978 mmol) in 55 mL of dioxane at 90° C. is added 2-trimethylsilylethyl-N,N-diisopropyl-pseudourea. The resulting solution is refluxed for about 8 hours. After cooling the mixture is diluted with 50 mL of ethyl acetate, filtered, washed with saturated aqueous sodium bicarbonate followed by brine, dried over magnesium sulfate, and concentrated. The resulting residue is chromatographed on silica gel (9/1 hexanes/ethyl acetate) to give the title compound as an oil: 2.24 g, 72% yield. 1H NMR (300 MHz, CDCl3): 7.32 (d, J=8.8, 2 H), 6.89 (d, J=8.8, 2 H), 5.08 (d, J=5.6, 1 H), 4.38-4.17 (m, 2 H), 3.81 (s, 3 H), 3.41 (d, J=5.6, 1 H), 0.96 (m, 2 H), 0.01 (s, 9 H).

Aufarbeitung

  1. temperatureThe resulting solution is refluxed for about 8 hours
  2. temperatureAfter cooling the mixture
  3. filtrationfiltered
  4. washwashed with saturated aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue is chromatographed on silica gel (9/1 hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-037917923f3e438fbf6b7a03f3e88f07
Quelldatensatz
uspto-grants-1992_02
Patentnummer
US05087631

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