Propylamine → HCID 86752752, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyldimethylsilylacetylene (14.5 g, 103 mmol, 1 equiv), n-propyl amine (42.5 ml,, 517 mmol, 5.00 equiv), and (Z)-1,2-dichloroethene (32.5 mL, 413 mmol, 4.00 equiv) in ether (150 mL) was deoxygenated at -78° C. by alternately evacuating the reaction vessel and flushing with argon (8×). The deoxygenated solution was transferred to an ice bath and copper iodide (2.95 g, 15.5 mmol, 0.15 equiv) was added. The mixture was cooled to -78° C. and was deoxygenated as above. In a similar fashion, bis(triphenylphosphine)palladium(II) chloride (3.64 g, 5.17 mmol, 0.05 equiv) was added at 0° C. and the reaction solution was deoxygenated at -78° C. The deoxygenated reaction mixture was warmed to 23° C. and was stirred at that temperature for 3 h. The product solution was washed with 1:1 saturated aqueous potassium carbonate solution:saturated aqueous ammonium chloride solution (3×150 mL), was dried over sodium sulfate, and was concentrated. The residue was purified by distillation under reduced pressure (bp 60°-65° C., mmHg) to afford (Z)-1-chloro-4-(tert-butyldimethylsilyl)-1-buten-3-yne as a clear oil (12.5 g, 60%). ##STR28##

Provenance & Evidence