Carbon Dioxide → HCID 131728743, compound

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.

1. dry with materialA heat dried 250 mL three next round bottom flask
2. customwas equipped
3. temperatureThe mixture was cooled
4. customthe internal temperature below −60° C
5. additionwas added
6. customthe internal below −50° C
7. extractionextracted with Et2O (150 mL) (×3)
8. washwashed with brine, (150 mL)
9. dry with materialdried (Na2SO4)
10. customthe solvent was evaporated under reduced pressure

ORD record

ord-c1a9afed65864257888d053aa5e8f6d8

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07902252B2