Chlorotrimethylsilane → 2-Trimethylsilyloxy-1-tridecene

Temperature

10 °C

A solution of n-butyllithium (12.6 mL, 27.7 mmol, 2.2 M in hexane) was added dropwise via syringe to a cooled (-78° C.) solution of diisopropylamine (4.1 mL, 29 mmol) in dry THF (200 mL). The resulting solution was stirred (15 minutes -78° C.), then a solution of 2-tridecanone (5.0 g, 25 mmol) in dry THF (50 mL) was added dropwise via a drop-in funnel. The resulting mixture was stirred (30 minutes, -78° C.), then a solution of chlorotrimethylsilane (3.5 mL, 28 mmol) in dry THF (40 mL) was added in one portion. The dry ice bath was removed and the resulting mixture was warmed to 10° C., then quenched with saturated sodium bicarbonate (100 mL). Dichloromethane (400 mL) and water (80 mL) were added and the layers were separated. The organic layer was washed with brine (1×200 mL), dried (MgSO4), and concentrated in vacuo to yield 6.7 g (98%) of the title compound as a milky oil which was used without further purification.

1. stirringThe resulting mixture was stirred (30 minutes, -78° C.)
2. customThe dry ice bath was removed
3. customquenched with saturated sodium bicarbonate (100 mL)
4. additionDichloromethane (400 mL) and water (80 mL) were added
5. customthe layers were separated
6. washThe organic layer was washed with brine (1×200 mL)
7. dry with materialdried (MgSO4)
8. concentrationconcentrated in vacuo

ORD record

ord-9a46ce94aab24829bd649d99d25cdb08

Source dataset

uspto-grants-1992_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05162360