Hexane → Tetramethyl m-trimethylsilylphenyl-1-hydroxy-ethylidenebis(phosphonate)

Participants

Reaction Steps

To a solution of dimethyl m-trimethylsilylphenylacetylphosphonate (1.63 g, 5.0 mmol) in Et2O (10 cm3) was added a solution of dimethylphosphite (0.83 g, 7.5 mmol), dibutylamine (0.32 g, 2.5 mmol) and hexane (10 cm3) at 0° C. A white solid began to form after a few minutes. After 20 min the mixture was filtrated to give the title compound (1.34 g, 65%) as a white solid. Recrystallization was achieved by adding water (9.5 cm3) to a solution of the title compound (0.50 g) in acetic acid (0.5 cm3) and then leaving the resulting mixture for several days in the refrigerator. Filtration afforded the bisphosphonate (0.33 g, 66%) as white crystals.

Provenance & Evidence