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

Temperature

95 °C

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.

1. temperatureby heating
2. washby washing with water (twice), an aqueous saturated sodium hydrogen carbonate solution, water and saturated brine
3. dry with materialAfter drying with anhydrous magnesium sulfate
4. concentrationthe resultant product was concentrated under a reduced pressure
5. additionthe residue was treated with the column chromatography (420 g, n-hexane:ethyl acetate=1:0-6:1)

ORD record

ord-a349dad99a82466a85e79209b993dec1

Source dataset

uspto-grants-2000_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06049009