Hexane → HCID 15077041, compound

Temperature

-78 °C

Under argon atmosphere, a solution of n-butyllithium in hexane (1.71N, 29.8 ml, 0.051 mol) was dropwise added to a solution of dimethyl methylphosphonate (6.32 g, 0.051 mol) in anhydrous THF (120 ml) with stirring at -78° C., and the mixture was stirred for 30 minutes. At -78° C., a solution of ethyl 2-methyl-4-nonynoate (4.0 g, 0.02 mol) in anhydrous THF (10 ml) was dropwise added, and the mixture was stirred for 30 minutes. Acetic acid (3.1 ml) and water (20 ml) were then added to the reaction mixture at 0° C. After concentration, water (20 ml) was added to the residue and the resulting mixture was extracted with ethyl acetate (50 ml×2). The ethyl acetate layers were combined, washed with water (20 ml) and with brine (20 ml), and dried over anhydrous sodium sulfate to concentrate. Vacuum distillation of the residue (b.p.=128°-130° C. at 0.16 mmHg) gave dimethyl 3-methyl-2-oxo-5-decynylphosphonate as a colorless, transparent oil (4.75 g, 0.0173 mol, 85% yield). The structure of this product was confirmed by the following data.

1. stirringthe mixture was stirred for 30 minutes
2. stirringthe mixture was stirred for 30 minutes
3. concentrationAfter concentration, water (20 ml)
4. additionwas added to the residue
5. extractionthe resulting mixture was extracted with ethyl acetate (50 ml×2)
6. washwashed with water (20 ml) and with brine (20 ml)
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationto concentrate
9. distillationVacuum distillation of the residue (b.p.=128°-130° C. at 0.16 mmHg)

ORD record

ord-0583040c4cf74c37a96fbf456c345588

Source dataset

uspto-grants-1989_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04880939