2-Methyl-3-butyn-2-ol → HCID 59445912, compound

Temperature

-78 °C

A solution of 2-methyl-3-butyne-2-ol (25 g, 0.3 mol) in tetrahydrofuran (250 ml) is cooled to −78° C. under a nitrogen atmosphere and to this solution, n-butyl lithium (1.6 molar solution in hexanes, 372 ml, 0.59 mol) is added slowly over 1.5-2.0 hours. The reaction mixture is stirred for 1 hour at −78° C. and a solution of methoxyacetone (38 g, 0.43 mol) in tetrahydrofuran (50 ml) is added. The reaction mixture is stirred at −78° C. for one hour, allowed to come to ambient temperature, and stirred for 2-3 hours. The reaction mixture is cooled to 10° C. and quenched with ice cold water. The mixture is extracted with ethyl acetate (3×250 ml), and 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. The residue is purified by column chromatography on silica gel to give 1-methoxy-2,5-dimethylhex-3-yne-2,5-diol (15 g) as a colourless oil.

1. additionis added slowly over 1.5-2.0 hours
2. stirringThe reaction mixture is stirred at −78° C. for one hour
3. customto come to ambient temperature
4. stirringstirred for 2-3 hours
5. temperatureThe reaction mixture is cooled to 10° C.
6. customquenched with ice cold water
7. extractionThe mixture is extracted with ethyl acetate (3×250 ml)
8. washwashed with water
9. dry with materialdried over anhydrous sodium sulfate
10. filtrationThe mixture is filtered
11. customthe filtrate is evaporated under reduced pressure
12. customThe residue is purified by column chromatography on silica gel

ORD record

ord-ea1b2174633e4a91bae731d3e8590d84

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895761B2