Methyl iodide → Nonanoic acid, 2-methyl-, ethyl ester

Temperatur

-78 °C

To a solution of diisopropylamine (9.0 ml, 64.4 mmol) in 100 ml anhydrous THF was added dropwise n-butyl lithium (1.61N, 40.0 ml, 64.4 mmol) at -78° C. under argon atmosphere. The mixture was stirred at -78° C. for 30 minutes and ethyl nonanoate (10.00 g, 53.7 mmol) was added dropwise. After stirring the mixture at -78° C. for 30 minutes, a solution of methyl iodide (3.7 ml, 59.1 mmol) in HMPA (2.8 ml, 16.1 mmol) was added dropwise and the mixture was stirred at -78° C. for 3.5 hours. Saturated aqueous solution of ammonium chloride (20 ml) was added to the reaction mixture and the resulting mixture was then extracted with ether (50 ml×4). The ether layers were washed with water (50 ml) and with brine (50 ml), dried over anhydrous sodium sulfate, and concentrated. Distillation gave yellow liquid, ethyl 2-methylnonanoate (9.6892 g, yield: 90.1%, b.p.: 63°-64° C./0.7 mmHg). The structure of this product was confirmed by the following data.

1. stirringAfter stirring the mixture at -78° C. for 30 minutes
2. stirringthe mixture was stirred at -78° C. for 3.5 hours
3. extractionthe resulting mixture was then extracted with ether (50 ml×4)
4. washThe ether layers were washed with water (50 ml) and with brine (50 ml)
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated
7. distillationDistillation

ORD-Eintrag

ord-421fce2b771c421085df4835a330aee7

Quelldatensatz

uspto-grants-1988_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04775692