Propargyl bromide → 13397-78-9

Participants

Reaction Steps

To a suspension of aluminum (20.87 g, 773 mmol) and mercury(II) chloride (1.187 g, 4.37 mmol) in ether (40 mL) was added triethoxymethane (49.8 g, 336 mmol) in ether (160 mL) over 60 minutes (internal temperature monitored and addition slowed to keep below 41° C.). The mixture was stirred at reflux for one hour, then brought to −78° C. in a dry ice/acetone bath. 3-bromoprop-1-yne (75 g, 504 mmol) in ether (17 mL) was added dropwise and the suspension was stirred at −78° C. for three additional hours. The reaction was quenched with water (300 mL) followed by 1N NaOH (120 mL). The layers were separated and the aqueous layer washed with additional diethyl ether. The organic extracts were dried over magnesium sulfate and concentrated to yield 4,4-diethoxybut-1-yne.

Provenance & Evidence