Chlorotrimethylsilane → HCID 57812298, compound

General Procedure BB: To a mixture of zinc (0.60 g, 9.2 mmol) in THF (1 mL) was added 1,2-Dibromoethane (0.03 mL, 0.3 mmol). The resulting mixture was stirred under reflux for 15 min and then cooled to rt. To the reaction mixture was added TMSCl (0.03 mL, 0.2 mmol) and THF (5 mL). A solution of propargyl bromide (0.750 mL, 8.42 mmol) and THF (3 mL) was then added dropwise to the reaction mixture over a 30 min period at −10° C. After 1 h, 2,6-Dichlorobenzaldehyde (1.46 g, 8.33 mmol) was added to the reaction mixture and allowed to warm to rt and stirred for 36 h. The reaction mixture was quenched with 1 M aqueous HCl (15 mL) and the organic layer was washed with brine (10 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to yield a dark yellow oil. The crude product was purified by silica gel chromatography using Hexane/EtOAc (80:20) as eluent to yield the desired product as a yellow oil. 1H NMR (CDCl3, 400 MHz): δ=2.03-2.06 (m, 1H), 2.82-2.90 (m, 1H), 3.00-3.07 (m, 1H), 3.09 (d, J=9.1 Hz, 1H), 5.67 (td, J=8.8, 6.6 Hz, 1H), 7.14-7.21 (m, 1H), 7.32 (d, 2H).

1. temperatureunder reflux for 15 min
2. temperatureto warm to rt
3. stirringstirred for 36 h
4. customThe reaction mixture was quenched with 1 M aqueous HCl (15 mL)
5. washthe organic layer was washed with brine (10 mL)
6. dry with materialThe organic layer was dried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. customto yield a dark yellow oil
9. customThe crude product was purified by silica gel chromatography

ORD record

ord-c5f23a8251a14fcdae9416786376b0e4

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08022206B2