Carbon Dioxide → HCID 131728743, compound

Participants

Reaction Steps

A heat dried 250 mL three next round bottom flask was equipped with stir bar, thermometer, septum and nitrogen inlet. This flask was then charged with trimethyl-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-silane, (30 mmol) and dry THF, (40 mL). The mixture was cooled using a dry ice/acetone bath and t-BuLi, (1.7 M in pentane, 19 mL, 33 mmol) was added dropwise, keeping the internal temperature below −60° C. The mixture was held in the dry ice bath for 1 h and then the alk-2-en-1-ol (i.e., cinnamyl bromide, where R=Ph), (5.3 mL, 36 mmol) dissolved in 5 mL of THF was added keeping the internal below −50° C. The mixture was held for approximately 1 h in the dry ice bath, and then allowed to warm to room temperature. The reaction mixture was added to saturated NH4Cl, (250 mL), extracted with Et2O (150 mL) (×3), washed with brine, (150 mL), dried (Na2SO4) and the solvent was evaporated under reduced pressure to give the desired trimethyl(6-alk-3-(tetrahydro-2H-pyran-2-yloxy)hex-5-en-1-ynyl)silane (i.e., trimethyl-[(E)-(6-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)hex-5-en-1-ynyl)silane, where R=Ph). The material was used in the next step without characterization or purification.

Provenance & Evidence