Reaktion #475925

Reaktionsgleichung

tert-butyldimethylsilyl chloride

compound

(1R,2R,4R,6S)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-ol

imidazole

water

→

titled compound

Ausbeute 91.0%

tert-butyl{[(1S,2R,4S,6S)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]hept-2-yl]oxy}dimethylsilane

Ausbeute 91.0%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe resulting layers were separated
2. 2
   ExtraktionThe aqueous layer was extracted three times with 120 mL each of tert-butyl methyl ether
3. 3
   Waschenwashed twice with 125 mL each of 10% aqueous NaCl
4. 4
   TrocknenThe tert-butyl methyl ether solution was dried over MgSO4
5. 5
   Filtrationthen filtered
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe product was purified on 2.00 kg of Silica Gel 60 with a gradient of hexanes

Vorschrift

The compound of Example 16A (11.0 g, 65 mmol) in 66 mL of dimethylformamide was treated with 5.37 g (1.2 equivalents) of imidazole followed by 11.2 g (1.14 equivalents) of tert-butyldimethylsilyl chloride. The reaction was stirred for 20 hours at ambient temperature. The reaction solution was mixed with 200 mL of water and the resulting layers were separated. The aqueous layer was extracted three times with 120 mL each of tert-butyl methyl ether. The organic layers were combined, and washed twice with 125 mL each of 10% aqueous NaCl. The tert-butyl methyl ether solution was dried over MgSO4 then filtered and concentrated in vacuo. The product was purified on 2.00 kg of Silica Gel 60 with a gradient of hexanes:tert-butyl methyl ether from 19:1 (8 L) to 9:1 (4 L) to afford 16.2 the titled compound (16.2 g, 91 %).

Quelle