Propargyl bromide → 13397-78-9

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.

1. addition(internal temperature monitored and addition slowed to keep below 41° C.)
2. temperatureat reflux for one hour
3. custombrought to −78° C. in a dry ice/acetone bath
4. stirringthe suspension was stirred at −78° C. for three additional hours
5. customThe reaction was quenched with water (300 mL)
6. customThe layers were separated
7. washthe aqueous layer washed with additional diethyl ether
8. dry with materialThe organic extracts were dried over magnesium sulfate
9. concentrationconcentrated

ORD record

ord-fb1b706084ad4ad8b4691ea76137b6f0

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691838B2