2-Bromo-2-methylpropanoyl cyanide → 5-(4-(benzyloxy)phenyl)-4-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one

To a pre-cooled 0° C. solution of 1-(4-(benzyloxy)phenyl)-2-(4-methoxyphenyl)-ethanone (2 g, 6.02 mmol) in THF (20 mL) under an inert atmosphere was added t-BuOK (8 mL, 1.0 N solution in THF). The mixture was then stirred for 30 minutes. 2-Bromo-2-methylpropanoyl cyanide (2 g, 12 mmol) was then added to then reaction mixture and stirring was continued for an additional 16 h. The reaction mixture was then quenched with cold water (10 mL) and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water (30 mL) and brine (30 mL), and then dried over Na2SO4 concentrated and purified via silica gel column chromatography (10-15% Ethyl acetate in hexanes) to afford 5-(4-(benzyloxy)phenyl)-4-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (100 mg) as a white solid.

1. customreaction mixture
2. stirringstirring
3. waitwas continued for an additional 16 h
4. customThe reaction mixture was then quenched with cold water (10 mL)
5. extractionextracted with EtOAc (2×50 mL)
6. washThe combined organic layers were washed with water (30 mL) and brine (30 mL)
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. custompurified via silica gel column chromatography (10-15% Ethyl acetate in hexanes)

ORD record

ord-7e059ed7c4c14b54ae4319bb9775bd29

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466148B2