Ethyl vinyl ether → HCID 22227318, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl vinyl ether (19.47 g, 270 mmol) in THF was added 106 mL of tert-butyl lithium (1.7 M, 180 mmol) dropwise at −78° C. The solution was warmed to 0° C. with an ice bath, stirred for another one hour and then re-cooled to −78° C. To this lithiated enol ether was added dropwise a solution of 5-methoxymethoxy-2-pentanone (13.16 g 90 mmol) in 10 mL of THF. The resulting mixture was stirred for one hour at −78° C. and one and a half hour at 0° C., and then slowly warmed up to room temperature. The reaction mixture was quenched with 70 mL of saturated NH4Cl aq. The organic layer was separated and the aqueous layer was extracted with 3×100 mL of diethyl ether. The combined organic layer was dried over Na2SO4 and concentrated via rotary evaporation to afford 2-ethoxy-3-hydroxy-6-methoxymethoxy-3-methyl-1-hexene in quantitative yield (19.4 g). The crude product was used in the subsequent reaction without further purification.

Provenance & Evidence