Sulfuric Acid → Dimethyl (3-fluoro-2-oxoheptyl)phosphonate

Participants

Reaction Steps

To a solution of 7.7 g. (0.06 mole) of dimethyl methyl-phosphonate in 80 ml. of tetrahydrofuran at -73° C. was added dropwise 43.4 ml. of a 1.42 molar solution of butyl lithium in hexane. After stirring for 5 minutes, a solution of 4 g. (0.03 mole) of ethyl 2-fluorohexanoate in 20 ml. of tetrahydrofuran was added dropwise. The resulting solution was then allowed to warm to 0° and then acidified (pH3) with 2 N sulfuric acid. The mixture was then extracted with hexane, the hexane solution washed with a saturated sodium chloride solution and then dried (MgSO4). The solvent was then removed under reduced pressure and the residue distilled to give 5.8 g of dimethyl(2-oxo-3-fluoroheptyl)phosphonate, b.p. 116°-118°/0.4 mm.

Provenance & Evidence