Hexane → HCID 21290102, compound

Temperature

0 °C

n-Butyl lithium in hexane (1.59N, 63.3 ml, 0.1 mol) was added dropwise under argon atmosphere with stirring to a solution of dimethyl methylphosphonate (12.4 g, 0.1 mol) in anhydrous THF (80 ml) at -78° C., and stirred for 30 min. To the reaction mixture was added dropwise a solution of methyl 2,2-dimethyl-4-oxaheptylate (7.0 g, 0.04 mol) in anhydrous THF (10 ml). The mixture was stirred for 30 min. and allowed to warm to 0° C. To the resulting mixture were added acetic acid (6.2 ml) and water (10 ml), and the mixture was concentrated. Water (20 ml) was added to the residue and the mixture was extracted with ethyl acetate (50 ml×2). The ethyl acetate layers were washed with water (20 ml) and with brine (20 ml), dried over anhydrous sodium sulfate, and concentrated to afford the residue. Column chromatography (silica gel; 200 g, ethyl acetate/cyclohexane: 2/1) of the residue gave a colourless and transparent oil of dimethyl 3,3-dimethyl-2-oxo-5-oxaoctylphosphonate (6.15 g, 0.023 mol, yield: 57.5%). The product was assigned the structure by the following data.

1. stirringThe mixture was stirred for 30 min.
2. concentrationthe mixture was concentrated
3. additionWater (20 ml) was added to the residue
4. extractionthe mixture was extracted with ethyl acetate (50 ml×2)
5. washThe ethyl acetate layers were washed with water (20 ml) and with brine (20 ml)
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated
8. customto afford the residue

ORD record

ord-19bedc4fe6bc45c7bd0a64dcefab1c30

Source dataset

uspto-grants-1988_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04775692