Imidazole → 3-(tert-Butyldimethylsiloxy)butyric acid methyl ester

HRID 1090326Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1090326
[OH:1][CH:2]([CH3:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5].N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>CN(C=O)C>[Si:14]([O:1][CH:2]([CH3:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 15146Methyl 3-hydroxybutyrateHCID 28928tert-Butyldimethylsilyl chloride

Produkt 1

HCID 137127793-(tert-Butyldimethylsiloxy)butyric acid methyl esterAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5.91 Grams (50 mmol) of methyl 3-hydroxybutyrate and 3.74 g (55 mmol) of imidazole were dissolved in 20 ml of DMF and thereto 8.29 g (55 mmol) of t-butyldimethylsilylchloride was added in several portions. After stirring the mixture at room temperature for 30 minutes, ice water was added and extraction with diethyl ether was conducted three times. The extract was washed with a saturated solution of NaCl, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate was distilled (62° to 68° C./5 mmHg) to give 10.51 g of methyl (-)-3-t-butyldimethylsilyloxybutyrate (yield: 91%).

Aufarbeitung

  1. extractionextraction with diethyl ether
  2. washThe extract was washed with a saturated solution of NaCl
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. distillationThe concentrate was distilled (62° to 68° C./5 mmHg)

Quellen und Nachweise

ORD-Eintrag
ord-f7f7f5c7be3f412ebde8b808fdf00c0f
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05081238

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