Diethyl Ether → (E)-4-(tert-butylthio)-3-buten-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of (E)-4-methoxy-3-buten-2-one (purity: 90%, 7.92 ml, 69.9 mmol) and tert-butylmercaptan (5.54 ml, 48.9 mmol) in carbon tetrachloride (70 ml) was added, under ice cooling, trifluoroacetic acid (7.54 ml, 97.9 mmol), followed by heating, under reflux, on an oil bath at 95° C. for 4 hours. After ice cooling, ethyl ether was added 5 thereto, followed by washing with water (twice), an aqueous saturated sodium hydrogen carbonate solution, water and saturated brine. After drying with anhydrous magnesium sulfate, the resultant product was concentrated under a reduced pressure and the residue was treated with the column chromatography (420 g, n-hexane:ethyl acetate=1:0-6:1) to thereby obtain the titled compound in the form of a pale yellow oil.

Provenance & Evidence