Methyl iodide → 5183-61-9

Temperature

5 °C

To a suspension of sodium hydride (5.0 g, 0.125 mol) in tetrahydrofuran (250 mL) was added a solution of ethyl 2-oxocyclohexanecarboxylate (19.9 mL, 0.125 mol) in tetrahydrofuran (30 mL) whilst maintaining the temperature of the mixture between 10° C. and 15° C. by means of an ice bath. After stirring at 5° C. for 1 hour, butyl lithium (52.5 mL, 2.5 M solution in hexanes, 131 mmol) was added dropwise while maintaining the temperature below 12° C. After stirring at 5° C. for 30 minutes, iodomethane (7.8 mL, 125 mmol) was added. The reaction mixture was stirred at 5° C. for 1.5 hours and then quenched with a saturated solution of ammonium chloride. The mixture was diluted with ethyl ether, washed with water. The organic extracts were dried over magnesium sulfate and concentrated. The resulting residue was distilled (100–110° C., 0.1 torr) to obtain the title compound as a colorless oil.

1. temperaturewhilst maintaining the temperature of the mixture between 10° C. and 15° C. by means of an ice bath
2. temperaturewhile maintaining the temperature below 12° C
3. stirringAfter stirring at 5° C. for 30 minutes
4. stirringThe reaction mixture was stirred at 5° C. for 1.5 hours
5. customquenched with a saturated solution of ammonium chloride
6. additionThe mixture was diluted with ethyl ether
7. washwashed with water
8. dry with materialThe organic extracts were dried over magnesium sulfate
9. concentrationconcentrated
10. distillationThe resulting residue was distilled (100–110° C., 0.1 torr)

ORD record

ord-2afc76b8c8a04ac2b47c2c5bd71a3bee

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07157475B2