Diisopropylethylamine → HCID 20578892, Verbindung

HRID 1760130Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1760130
[CH3:1][O:2][C:3](=[O:9])[C@@H:4]([OH:8])[CH:5]([CH3:7])[CH3:6].C(N(C(C)C)CC)(C)C.[CH3:19][Si:20]([CH3:27])([CH3:26])[CH2:21][CH2:22][O:23][CH2:24]Cl>ClCCl>[CH3:1][O:2][C:3](=[O:9])[C@@H:4]([O:8][CH2:24][O:23][CH2:22][CH2:21][Si:20]([CH3:27])([CH3:26])[CH3:19])[CH:5]([CH3:7])[CH3:6]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 11194352Methyl (2S)-2-hydroxy-3-methylbutanoate

Produkt 1

HCID 20578892HCID 20578892, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of methyl-2-(S)-hydroxy-3-methylbutanoate (1.0 eq; J. Org. Chem. (1997), 62(7), 2292-2297, incorporated herein by reference) in dichloromethane was stirred with diisopropylethylamine (2.0 eq) under nitrogen. 2-Trimethylsilylethoxymethyl chloride (3 eq; Aldrich) was added dropwise via syringe. The solution was stirred at room temperature for 17 hours. The solution was washed with 1.0N HCl, and the water layer was back extracted with dichloromethane. The organics were combined, dried over Na2SO4, and the solvents removed in vacuo. The residue was purified via radial chromatography using 20% ethyl acetate in hexanes affording the title intermediate as a clear oil.

Aufarbeitung

  1. washThe solution was washed with 1.0N HCl
  2. extractionthe water layer was back extracted with dichloromethane
  3. dry with materialdried over Na2SO4
  4. customthe solvents removed in vacuo
  5. customThe residue was purified via radial chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c3bdbcea58f6429ebe90ab90c6fc7570
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06838455B2

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