反应详情

温度

0 °C

Combine 1-Methyl-cyclopropanecarbaldehyde (4.88 g, 58.01 mmol) and methyldichloroacetate (5.46 mL, 52.74 mmol) in diethyl ether (20 mL); cool to 0° C. Add dropwise a solution of sodium (1.21 g, 52.74 mmol) in methanol (20 mL). Stir the reaction mixture for 4 hours at 0° C. under N2. Extract the mixture with diethyl ether versus water. Dry the resulting organics over magnesium sulfate, filter, and concentrate to a clear liquid. Combine the liquid with thiourea (4.42 g, 58.01 mmol) in methanol (25 mL). Heat the reaction mixture for 14 hours at 60° C. under N2. Concentrate in vacuo and purify on a plug of silica gel, eluting with hexanes→3% methanol in dichloromethane→5% methanol in dichloromethane to afford product (5.10 g, 46% over two steps). MS (ES), m/z 213 (M+1).

1. extractionExtract the mixture with diethyl ether versus water
2. dry with materialDry the resulting organics over magnesium sulfate
3. filtrationfilter
4. concentrationconcentrate to a clear liquid
5. temperatureHeat the reaction mixture for 14 hours at 60° C. under N2
6. concentrationConcentrate in vacuo
7. custompurify on a plug of silica gel
8. washeluting with hexanes→3% methanol in dichloromethane→5% methanol in dichloromethane
9. customto afford product (5.10 g, 46% over two steps)