Imidazole → (S)-2-(tert-Butyldimethylsilyloxy)-g-butyrolactone

HRID 395915

Reaktionsgleichung

O[C@@H:2]1[CH2:7][O:6][C:4](=[O:5])[CH2:3]1.N1C=CN=C1.[CH3:13][C:14]([Si:17](Cl)([CH3:19])[CH3:18])([CH3:16])[CH3:15].CN(C=[O:25])C>>[CH3:13][C:14]([Si:17]([CH3:19])([CH3:18])[O:25][C@H:3]1[CH2:2][CH2:7][O:6][C:4]1=[O:5])([CH3:16])[CH3:15]

Komponenten

Edukt 4

HCID 795Imidazole

HCID 6228Dimethylformamide

HCID 28928tert-Butyldimethylsilyl chloride

HCID 72693893-Hydroxybutyrolactone, (3S)-

Produkt 1

HCID 10965951(S)-2-(tert-Butyldimethylsilyloxy)-g-butyrolactone

Versuchsvorschrift

3.92 g (38.4 mmol) of (S)-3-hydroxybutyrolactone with 5.23 g (2 equivalents, 76.8 mmol) of imidazole are introduced at 0° C. into 50 ml of absolute DMF. 7.53 g (1.3 equivalents, 49.92 mmol) of TBSCl is now slowly added and stirred for 2.5 hours.

Quellen und Nachweise

ORD-Eintrag: ord-6a09d1ba34d54481a03948cc134cebb3
Quelldatensatz: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06605726B1

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