Hexane → HCID 14302179, compound

Temperature

-78 °C

Dimethyl methylphosphonate (5.89 g, 47.5 mmol) was dissolved in anhydrous THF (80 ml). To the resulting solution cooled to -78° C. under argon atomosphere, a solution of n-butyl lithium in hexane (1.63N, 29.1 ml, 47.5 mmol) was added and the mixture was stirred for 30 minutes. A solution of methyl 4,4-dimethylhexanoate (3.00 g, 19.0 mmol) in anhydrous THF (15 ml) was then added to the reaction mxiture at -78° C. and the mixture was stirred for 30 minutes. After warming the mixture to room temperature, acetic acid was added to neutralize the solution and a small quantity of water was then added, and concentrated. After ethyl acetate was added to the residue, the ethyl acetate layer was washed with water and with brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was distilled under reduced pressure to give oily product, dimethyl 5,5-dimethyl-2-oxoheptylphosphonate (3.38 g, 13.5 mmol, 71.1%, b.p.: 120°-122° C./0.18 mmHg). The structure was confirmed by the following data.

1. stirringthe mixture was stirred for 30 minutes
2. temperatureAfter warming the mixture to room temperature
3. concentrationconcentrated
4. additionAfter ethyl acetate was added to the residue
5. washthe ethyl acetate layer was washed with water and with brine
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated
8. distillationThe residue was distilled under reduced pressure

ORD record

ord-3f94f3d776d047d6a27038c9b2b97271

Source dataset

uspto-grants-1988_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04775692