Hexane → HCID 21290102, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence