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

Participants

Reaction Steps

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%).

Provenance & Evidence