2-methyl-2-(methylsulfonyl)propanenitrile synthesis
- Product Name:2-methyl-2-(methylsulfonyl)propanenitrile
- CAS Number:14668-29-2
- Molecular formula:C5H9NO2S
- Molecular Weight:147.2
Yield:14668-29-2 93%
Reaction Conditions:
Stage #1: methanesulfonyl-acetonitrilewith sodium hydride in tetrahydrofuran;mineral oil at 0; for 0.333333 h;
Stage #2: methyl iodide in tetrahydrofuran;mineral oil at 0 - 25; for 21.5 h;
Steps:
1.1
To a stirred solution of the commercially available 2-(methylsulfonyl)- acetonitrile (1 1.9 g, 100 mmol) in 300 mL of THF was added NaH (8.0 g, 60% in mineral oil, 200 mmol) slowly at 0 °C. After 20 min, Mel (28.4 g, 200 mmol) was added dropwise over a period of 1.5 h. The mixture was allowed to warm from 0 °C to room temperature overnight (20 h). It was quenched with H20 (250 mL), and the THF was evaporated. The aqueous solution was extracted with three 250 mL portions of ethyl acetate. The combined organic extracts were washed with brine (200 mL), and concentrated. Trituration of the residue with hexanes/ether gave 2-methyl-2-(methylsulfonyl)propanenitrile (13.6 g, 93%). 1H NMR (CDCI3 400 MHz) 5
References:
WO2012/139425,2012,A1 Location in patent:Page/Page column 74
10074-86-9
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14668-29-2
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