Chlorotrimethylsilane → HCID 11745995, compound

Temperature

-78 °C

Into a 1-L three neck round-bottom flask, was placed a solution of but-3-yn-1-ol (20.0 g, 285 mmol, 1.00 equiv) in tetrahydrofuran (300 mL) and the mixture was purged with nitrogen. The mixture was cooled to −78° C., then n-butyllithium (2.5 M in THF) (270 mL, 2.40 equiv) was added drop-wise followed by the addition of chlorotrimethylsilane (67.9 g, 625 mmol, 2.20 equiv). The resulting mixture was then stirred for 1 h at 25° C., then carefully quenched with aqueous sodium bicarbonate (250 mL). The aqueous was extracted with ether (3×100 mL) and the combined organics was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography with ether/petroleum ether (1:10-1:1) as the eluent to obtain the title compound as a colorless oil (10.0 g, 16%).

1. customthe mixture was purged with nitrogen
2. customcarefully quenched with aqueous sodium bicarbonate (250 mL)
3. extractionThe aqueous was extracted with ether (3×100 mL)
4. dry with materialthe combined organics was dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified by silica gel chromatography with ether/petroleum ether (1:10-1:1) as the eluent

ORD record

ord-22001b8503c94733a0b33d5290ac7528

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871790B2