1,1',1''-(Chlorosilylidyne)tris(benzene) → HCID 11655779, compound

Participants

Reaction Steps

A solution of triphenylsilyl chloride (0.337 g, 1.14 mmol) in dry pyridine (3 mL) was added drop-wise to a solution of 1-(6′-hydroxyhexyl)uracil (0.200 g, 0.94 mmol) in dry pyridine (4 mL) cooled in an ice-salt bath. The reaction mixture was kept at 0° C. under nitrogen for 3 h30. As TLC monitoring evidenced the presence of unreacted starting material, triphenylsilyl chloride (0.325 g, 1.10 mmol) in dry pyridine (1 mL) was added. After a further 45 min at 0° C., the reaction had reached completion and was quenched with CH3OH (0.1 mL). Removal of the solvent in vacuo afforded a crude yellow oil which was purified by silica gel chromatography using a Jones Chromatography Isolute SI column with a gradient elution of 0→5% CH3OH in CHCl3. The title compound was obtained as a white solid (0.140 g, 32%) from the fractions with Rf=0.52 (10% CH3OH/CHCl3). Some starting material (0.130 g, 65%) was also recovered, possibly resulting from hydrolysis during the work up.

Provenance & Evidence