反応 #475925

反応方程式

tert-butyldimethylsilyl chloride

compound

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

imidazole

water

→

titled compound

収率 91.0%

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

収率 91.0%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   その他the resulting layers were separated
2. 2
   抽出The aqueous layer was extracted three times with 120 mL each of tert-butyl methyl ether
3. 3
   洗浄washed twice with 125 mL each of 10% aqueous NaCl
4. 4
   乾燥The tert-butyl methyl ether solution was dried over MgSO4
5. 5
   ろ過then filtered
6. 6
   濃縮concentrated in vacuo
7. 7
   その他The product was purified on 2.00 kg of Silica Gel 60 with a gradient of hexanes

実験手順

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 %).

出典