tert-Butyl methyl ether → 4-(cis-3-Allylcyclohexyloxymethyl)-2-(3-methoxyphenyl)-5-methyloxazole

Participants

Reaction Steps

1.8 g of cis-3-allylcyclohexanol are dissolved in 20 ml of dimethyl-formamide, and 770 mg of sodium hydride (60% strength suspension in paraffin oil) are added. After 30 minutes, 4 g of 4-iodomethyl-5-methyl-2-(3-methoxyphenyl)oxazole, dissolved in 20 ml of dimethylformamide, are added dropwise. The mixture is stirred at room temperature for 1 hour. 200 ml of methyl tert-butyl ether are then added to the reaction mixture, and the mixture is washed three times with water. The organic phase is dried over MgSO4 and the solvent is then removed under reduced pressure. The residue is purified on silica gel using the mobile phase n-heptane:ethyl acetate=10:1. This gives 750 mg of 4-(cis-3-allyl-cyclohexyloxymethyl)-2-(3-meLhoxpheny,”-5-methyloxazole as an Oil. C21H27NO3 (341.45), MS(ESI): 342 (M+H+), Rf(n-heptane:ethyl acetate=2:1)=0.26.

Provenance & Evidence