Diethyl Ether → HCID 14639473, compound

In a 1-L three-neck round-bottom flask equipped with an efficient reflux condenser, a tru-bore mechanical stirrer equipped with a Teflon paddle and a pressure-equalizing addition funnel was placed cuprous chloride (0.65 g, 6.5 mmol), triethylamine (73.9 g, 0.73 mol) and diethyl ether (500 mL). Trichlorosilane (98.2 g, 0.73 mol), 1,4-dichloro-cis-2-butene (80.6 g, 0.65 mol) and diethyl ether (60 mL) were placed in the addition funnel. This solution was added to the vigorously stirred greenish suspension of cuprous chloride and triethylamine over a period of 4 h. The reaction mixture was stirred overnight. The triethylammonium hydrochloride salts were removed by filtration under argon. These were washed several times with pentane. The solvents were removed from the combined filtrate by distillation through a 15 cm vacuum-jacketed Vigreux column at atmosphere pressure. The residue was transferred to a 250-mL round-bottom flask. The product was purified by fractional distillation under reduced pressure. A fraction with b.p. 72°-73° C./2.8 mmHg, 78.2 g, 54% yield was isolated. It had the following spectral properties.

1. customIn a 1-L three-neck round-bottom flask equipped with an efficient reflux condenser, a tru-bore mechanical stirrer
2. customThe triethylammonium hydrochloride salts were removed by filtration under argon
3. washThese were washed several times with pentane
4. customThe solvents were removed from the combined filtrate by distillation through a 15 cm vacuum-jacketed Vigreux column at atmosphere pressure
5. customThe residue was transferred to a 250-mL round-bottom flask
6. distillationThe product was purified by fractional distillation under reduced pressure
7. customA fraction with b.p. 72°-73° C./2.8 mmHg, 78.2 g, 54% yield was isolated

ORD record

ord-defa86df65ee43b1a1ef09c327a9ee87

Source dataset

uspto-grants-1992_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05169916