Acetone → 2,2-Dimethyl-5-(2-(methylthio)ethyl)-4-oxazolidinone

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Reaction Conditions

Reaction Steps

In a 100 mL three-neck flask, 13.1 g of 96% strength 1-hydroxy-3-(methylthio)propanecarbonitrile (11) (0.1 mol) and 7.0 g of acetone (0.12 mol) were dissolved in 30 mL of glacial acetic acid at 10° C. Then, 5 mL of acetic anhydride (0.05 mol) were slowly added dropwise. Subsequently, a mixture of 10 mL of conc. sulfuric acid and 10 mL of glacial acetic acid was added slowly at 0° C. During this it must be ensured that the entire reaction solution does not become warmer than 0° C. This produced a viscous, yellowish, scarcely stirrable suspension. After addition was complete, the mixture was stirred for 1 h at 110° C. and subsequently 15 min at RT. The reaction solution was poured onto ice (approximately 150 g) and thereafter extracted three times with 100 mL of diethyl ether each time. The ether phase was washed once with saturated sodium hydrogencarbonate solution and subsequently with saturated sodium chloride solution and dried over sodium sulfate. The Na2SO4 was filtered off and the ether was taken off in vacuum. This produced 4.5 g of an orange-brown oil which was recrystallized from n-hexane. After filtration and removal of final solvent residues in high vacuum, 2.8 g (14.8 mmol, M=189.28 g/mol, yield=15%) of 2,2-dimethyl-5-(2-(methylthio)ethyl)-4-oxazolidinone (10) were isolated as a slightly yellowish solid. The NMR data agreed with those of Example 10.

Provenance & Evidence