Butylamine → (Z)-5-chloro-1,1-diethoxy-4-pentene-2-yne

Temperature

25 °C

Neat cis-1,2-dichloroethylene (4.5 ml, 60 mmol) followed by butylamine (8.0 ml, 81 mmol) was added to a solution of copper iodide (0.90 g, 4.73 mmol) and palladium tetrakis(triphenylphosphine) (1 g, 0.86 mmol) in 40 mL of dry benzene stirring at 25° C. under argon. Immediately thereafter, a solution of 3,3-diethoxypropyne (5 g, 39 mmol) in 10 mL of benzene was added via cannula. The reaction vessel was wrapped in foil to shield it from light, and the reaction mixture was stirred for 4.2 h at 25° C. The dark brown reaction mixture was filtered by suction through a coarse frit and diluted to approximately 10 ml with diethylether. The solution was washed with 75 mL of water and 120 mL saturated brine, and the organic layer was dried over anhydrous Na2SO4 and then concentrated in vacuo. The residue was flash chromatographed on SiO2 using 5%, then 10%, and then 15% diethylether/pentane as eluent to provide the desired product as a clear liquid (3.9 g, 55%).

1. filtrationThe dark brown reaction mixture was filtered by suction through a coarse frit
2. additiondiluted to approximately 10 ml with diethylether
3. washThe solution was washed with 75 mL of water and 120 mL saturated brine
4. dry with materialthe organic layer was dried over anhydrous Na2SO4
5. concentrationconcentrated in vacuo
6. customchromatographed on SiO2 using 5%

ORD record

ord-be8b66aa9db9498490a387b0bc0dcc7f

Source dataset

uspto-grants-1994_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05318989