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HRID 388745Erstellt: 24. Oktober 2026

Imidazole → Tert-butyl(dimethyl)({(1s,2r,4s,6s)-1-methyl-4-[(triethylsilyl)oxy]-7-oxabicyclo[4.1.0]hept-2-yl}oxy)silane

https://huagongshe.com/de/reaction/388745

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktImidazoleHCID 795—
EduktWaterHCID 962—
EduktChlorotriethylsilaneHCID 13819—
Edukt(1s,3s,5r,6s)-5-{[Tert-butyl(dimethyl)silyl]oxy}-6-methyl-7-oxabicyclo[4.1.0]heptan-3-olHCID 87628830—
LösungsmittelDimethylformamideHCID 6228—
ProduktTert-butyl(dimethyl)({(1s,2r,4s,6s)-1-methyl-4-[(triethylsilyl)oxy]-7-oxabicyclo[4.1.0]hept-2-yl}oxy)silaneHCID 8753826299%

Reaktionsschritte

The compound of Example 16D (4.71 g, 18.2 mmol) and imidazole (1.76 g, 25.6 mmol, 1.4 equivalents) were dissolved in 36 mL of dimethylformamide. Then chlorotriethylsilane (3.34 g, 21.9 mmol) was added, and the reaction was stirred at ambient temperature for 2 hours. 125 mL of Water was added to the reaction mixture. Two layers of liquors were obtained and about 6 g of upper layer was separated. Then the lower aqueous layer was extracted three times with 100 mL each of tert-butyl methyl ether. The combined organic layers were washed with 125 mL of 10% aqueous NaCl, dried over MgSO4, filtered and concentrated in vacuo to afford the titled compound (6.71 g, 99%).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08377913B2
Quelldatensatzuspto-grants-2013_02
ORD IDord-f92a8ae7e6494eedb1f8edc7e8fae54c
Quellennotizuspto-grants-2013_02