2-Methyl-3-butyn-2-ol → 2-(1,1-Dimethylprop-2-ynyloxy)propionic acid methyl ester

Temperature

0 °C

To a mixture of sodium hydride (23.8 g, 0.595 mol) in tetrahydrofuran (400 ml) cooled to 0° C., is added a solution of 2-methyl-3-butyne-2-ol (50 g, 0.595 mol) in tetrahydrofuran (50 ml). The reaction mixture is stirred at 0° C. for 1 hour. A solution of methyl-2-bromo-propionate (99.36 g, 0.595 mol) in tetrahydrofuran (100 ml) is added to the reaction mixture slowly at 0° C. The reaction mixture is stirred at 0° C. for 2 hours and allowed to come to ambient temperature and stirred for 1 hour. The reaction mixture is cooled to 10° C. and quenched with ice cold water. The mixture is extracted with diethyl ether (3×200 ml), the organic phases are combined, washed with water, and dried over anhydrous sodium sulfate. The mixture is filtered and the filtrate is evaporated under reduced pressure to give 2-(1,1-dimethylprop-2-ynyloxy)propionic acid methyl ester (90 g) as a colorless oil, used without further purification in the next step.

1. stirringThe reaction mixture is stirred at 0° C. for 2 hours
2. customto come to ambient temperature
3. stirringstirred for 1 hour
4. temperatureThe reaction mixture is cooled to 10° C.
5. customquenched with ice cold water
6. extractionThe mixture is extracted with diethyl ether (3×200 ml)
7. washwashed with water
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationThe mixture is filtered
10. customthe filtrate is evaporated under reduced pressure

ORD record

ord-69b879a4537944f3951ba5106af4078f

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895761B2