4-hydroxy-benzyl acetate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.53 g (132 mmol) of 60% sodium hydride is added in portions to a solution at 0° C. of 20 g (120 mmol) of (4-hydroxy-phenyl)-methyl acetate diluted in 100 ml of tetrahydrofuran and 100 ml of dimethylformamide. The reaction mixture is stirred at room temperature, and then 15 ml (132 mmol) of 1-chloromethoxy-2-methoxy-ethane is added dropwise. After stirring at room temperature for 2 hours, then adding water, the reaction mixture is extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution and then dried over magnesium sulfate. After evaporation of the solvents, 25 g (86%) of [4-(2-methoxy-ethoxymethoxy)-phenyl]-methyl acetate is obtained in the form of a colorless oil. After stirring at room temperature for 2 hours adding water, the reaction mixture is extracted with ethyl acetate washed with saturated sodium chloride solution dried over magnesium sulfate After evaporation of the solvents

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-chloromethyl-2-(2-furyl)-5-methyloxazole (10.0 g), 4-hydroxyphenylmethyl acetate (8.41 g), potassium carbonate (14.0 g) and N,N-dimethylformamide (50 ml) was stirred at 70° C. for 1 hr. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and methyl [4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]phenyl]acetate (9.23 g, yield 56%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (2:3, volume ratio). the mixture was extracted with ethyl acetate The ethyl acetate layer was washed with saturated brine dried (MgSO4) concentrated