Tetrabutylammonium Fluoride → Ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoate

To a solution of ethyl 3-(3-(((tert-butyldiphenylsilyl)oxy)methyl)phenyl)-3-cyclopropylpropanoate (4.54 g) in THF (20 mL) was added a 1.0 M solution of tetrabutylammonium fluoride in THF (18.7 mL), and the mixture was stirred at room temperature for 4 hr. To the reaction mixture was added brine, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.94 g) as a colorless oil.

1. extractionthe mixture was extracted with ethyl acetate
2. dry with materialThe extract was dried over anhydrous sodium sulfate
3. customthe solvent was evaporated under reduced pressure
4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

ORD record

ord-c1b4e4c8ab7140f89f8b5484068abecc

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382188B2