2-Methyl-3-butyn-2-ol → 4-Hydroxy-1-(4-methoxyphenyl)-4-methylpent-2-yn-1-one

Temperature

-20 °C

To a stirred solution of 2-methylbut-3-yn-2-ol (2.15 g, 25.6 mmol) in dry THF (80 mL) was added n-BuLi (24.0 mL, 38.7 mmol, 1.6 M in hexane) drop wise at −20° C. under an inert atmosphere for a period of 10 min. After being stirred for 30 min at −20° C., a solution of N,4-dimethoxy-N-methylbenzamide (2.5 g, 12.8 mmol) in dry THF (10 mL) was added to reaction mixture and stirring was continued for an additional 3 h at −20° C. The reaction mixture was quenched with a saturated NH4Cl solution and extracted with EtOAc (2×100 mL). The combined organic layer was washed with water (100 mL), brine (40 mL), dried over Na2SO4, filtered and concentrated in vacuo to afford 4-hydroxy-1-(4-methoxyphenyl)-4-methylpent-2-yn-1-one (2.25 g, 81%) as a colorless liquid.

1. stirringstirring
2. waitwas continued for an additional 3 h at −20° C
3. customThe reaction mixture was quenched with a saturated NH4Cl solution
4. extractionextracted with EtOAc (2×100 mL)
5. washThe combined organic layer was washed with water (100 mL), brine (40 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-c387af050c57463bb4781fbf52993b46

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08343973B2