Methyl iodide → HCID 14302185, compound

Temperature

-78 °C

To a solution of diisopropylamine (8.9 ml, 63.3 mmol) in 100 ml of anhydrous THF was added dropwise n-butyl lithium (1.59N, 39.8 ml, 63.3 mmol) at -78° C. under argon atmosphere. After the mixture was stirred at -78° C. for 30 minutes, methyl 3-cyclohexyl-2-methylpropionate (7.7829 g, 42.2 mmol) was added dropwise. After the mixture was stirred at -78° C. for 30 minutes, a solution of methyl iodide (3.9 ml, 63.3 mmol) in HMPA (2.2 ml, 12.7 mmol) was added dropwise. After being stirred at -78° C. for 1 hour, the reaction mixture was diluted with an aqueous saturated solution of ammonium chloride. The aqueous mixture was extracted with ether (50 ml×4). Then, the combined ether layers were washed water (50 ml) and brine (50 ml), dried over anhydrous sodium sulfate, and concentrated. The residue was distilled to give a colorless liquid of methyl 3-cyclohexyl-2,2-dimethylpropionate (5.7294 g, yield 52.2%, b.p. 121.5°-123° C./22 mmHg), which was assigned the structure by the following data:

1. stirringAfter the mixture was stirred at -78° C. for 30 minutes
2. stirringAfter being stirred at -78° C. for 1 hour
3. extractionThe aqueous mixture was extracted with ether (50 ml×4)
4. washThen, the combined ether layers were washed water (50 ml) and brine (50 ml)
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated
7. distillationThe residue was distilled

ORD record

ord-69ea019ac0a54cb590340f599c34ba48

Source dataset

uspto-grants-1988_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04775692