2,4,6-Trimethylpyridine → HCID 18957432, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of dimethyl[1-hydroxy-(E,E)-5,9,13-trimethyl-4,8,12-tetradecatrienyl]-phosphonate (98 mg, 0.253 mmol) and 2,4,6-collidine (0.134 ml, 1.014 mmol) in dichloromethane (3 ml) under argon at 0° C., was added trimethylsilyl bromide (0.134 ml, 1.013 mmol) and the resulting mixture stirred at 0° C. for 30 min. and then at r.t. for 5 hr. The resulting white suspension was diluted with toluene (10 ml) and the solvent evaporated in vacuo, the resulting white solid was dissolved in ethylacetate and water and the pH was adjusted to 3 by the addition of 1M HCl solution. The organic layer was separated, dried (Na2SO4) and evaporated to afford a glassy residue. The solid was washed with acetonitrile (2×5 ml) and the white solid filtered off and dried in vacuo to afford the title compound.

Provenance & Evidence