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 minutes at −78° C. The reaction mixture was further stirred at this temperature for 20 minutes. A solution of (4-fluoro-phenyl)-(4-hydroxy-phenyl)-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. over 5 hours. The reaction mixture was quenched with saturated ammonium chloride solution, extracted into EtOAc and washed with dilute ammonium chloride solution. The organic layer was dried over magnesium sulfate. The solvent was removed under vacuum, and the resulting product was flash chromatographed on silica gel, giving M1.1 as an oil.

1. waitThe reaction mixture was brought to 0° C. over 5 hours
2. customThe reaction mixture was quenched with saturated ammonium chloride solution
3. extractionextracted into EtOAc
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
7. customchromatographed on silica gel
8. customgiving M1.1 as an oil

ORD record

ord-c3b17590bdc5410d85a69b887de178d7

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582803B2