Tetrabutylammonium Fluoride → Methyl 2-(2-ethynylphenyl)acetate

TBAF (1.0 M in THF; 28.5 mL, 28.5 mmol) was added to a solution of methyl 2-(2-((trimethylsilyl)ethynyl)phenyl)acetate (I2) (4.63 g, 19.0 mmol) in DCM (200 mL) at 0° C. The solution was stirred at room temperature for 1 hour before washing with 10% aqueous NaHCO3 (100 mL). The organic layer was dried (MgSO4) before removing the volatiles in vacuo to give a dark brown/black residue which was adsorbed onto silica gel and purified by column chromatography (Biotage Isolera, 0-10% EtOAc in petroleum benzine 40-60° C.) to give the title compound K1 as a red liquid (2.76 g, 83%); 1H NMR (400 MHz, CDCl3) δ 7.52 (dd, J=7.6, 1.1 Hz, 1H), 7.43-7.16 (m, 3H), 3.88 (d, J=9.6 Hz, 2H), 3.77-3.52 (m, 3H), 3.28 (s, 1H).

1. washbefore washing with 10% aqueous NaHCO3 (100 mL)
2. dry with materialThe organic layer was dried (MgSO4)
3. custombefore removing the volatiles in vacuo
4. customto give a dark brown/black residue which
5. custompurified by column chromatography (Biotage Isolera, 0-10% EtOAc in petroleum benzine 40-60° C.)

ORD record

ord-597d0c6dbeda435689876a936a2bd870

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266864B2