Ethyl trimethylsilylacetate → Ethyl 3-(4-fluorophenyl)-3-(4-hydroxyphenyl)-acrylate

A solution of lithium hexamethyldisilazide (23.1 mL, 1 M in THF) was added to a stirred solution of ethyl (trimethylsilyl)acetate (2.53 mL, 13.9 mmol) in THF (15 mL) in 10 min. at −78° C. The reaction mixture was further stirred at this temperature for 20 min. A solution of (4-fluorophenyl)-(4-hydroxyphenyl)-methanone (2 g, 9.2 mmol) in THF (30 mL) was slowly added to the reaction mixture. The reaction mixture was brought to 0° C. in 5 h. The reaction mixture was quenched with saturated ammonium chloride solution, extracted into ethyl acetate and washed with dilute ammonium chloride solution. The organic layer was dried over magnesium sulfate. The solvent was removed under vacuum and product was purified flash chromatography on silica gel, giving 45.1 as an oil (1.405 g).

1. waitThe reaction mixture was brought to 0° C. in 5 h
2. customThe reaction mixture was quenched with saturated ammonium chloride solution
3. extractionextracted into ethyl acetate
4. washwashed with dilute ammonium chloride solution
5. dry with materialThe organic layer was dried over magnesium sulfate
6. customThe solvent was removed under vacuum and product
7. customwas purified flash chromatography on silica gel

ORD record

ord-3db90a0cb721452bb57d31ec9e0cfb42

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07816367B2