Cyclohexanone → 1-(3-hydroxy-3-methylbut-1-ynyl)cyclohexanol

Temperature

-78 °C

A solution of 2-methyl-3-butyne-2-ol (25 g, 0.297 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, 410 ml, 0.65 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 cyclohexanone (46.2 ml, 0.44 mol) in tetrahydrofuran (46 ml) is added. The reaction mixture is stirred at −78° C. for one hour and allowed to come to ambient temperature and stirred at ambient temperature for 2-3 hours. The reaction mixture is cooled to 10° C. and quenched with ice cold water. The mixture is extracted with dichloromethane (3×250 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. The residue is purified by column chromatography on silica gel to give 1-(3-hydroxy-3-methylbut-1-ynyl)cyclohexanol (20 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 at ambient temperature 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 dichloromethane (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-9e077faabfd8415f9941fdbd21494e86

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895761B2