tert-Butyl methyl ether → Tert-butyl 2-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethoxy]-2-methylpropionate

Participants

Reaction Steps

50 mg of tert-butyl 2-(cis-3-hydroxycyclohexylmethoxy)-2-methylpropionate are dissolved in 0.5 ml of dimethylformamide and 22 mg of NaH (60%) are added. After 30 min of stirring, 112 mg of 5-methyl-2-p-tolyloxazol-4-yl-methyl iodide are added at room temperature. The mixture is placed in an ultrasonic bath for 10 min and then stirred at room temperature for 3 h. 10 ml of methyl tert-butyl ether and 10 ml of water are then added. The phases are separated, the aqueous phase is extracted once with methyl tert-butyl ether and the organic phases are dried over MgSO4 and concentrated. The residue is chromatographed on silica gel (heptane/ethyl acetate 5/1->1/1). 60 mg of the crude tert-butyl 2-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethoxy]-2-methylpropionate are obtained as a yellow oil. C27H39NO5 (457), LCMS(ESI): 458 (MH+).

Provenance & Evidence