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

Temperature

0 °C

A solution of TBAF (1 M solution in THF; 2.28 mL, 2.28 mmol) was added to a solution of methyl 2-(2-((trimethylsilyl)ethynyl)phenyl)propanoate (I50) (0.297 g, 1.14 mmol) in THF (10 mL) at 0° C. The reaction was stirred for 50 minutes at 0° C. then concentrated under reduced pressure and the residue taken up in EtOAc (20 mL). The organic solution was washed with saturated NaHCO3 (20 mL), water (20 mL) and dried over Na2SO4. The solvent was removed in vacuo to yield a brown oily residue. The oil was purified using column chromatography on silica gel (0-5% EtOAc in cyclohexane) to afford the title compound (I51) (0.192 g, 89%) as a pale yellow oil; 1H NMR (400 MHz, CDCl3) δ 7.53-7.48 (m, 1H), 7.36-7.28 (m, 2H), 7.24-7.20 (m, 1H), 4.31 (q, J=7.2 Hz, 1H), 3.67 (s, 3H), 3.28 (s, 1H), 1.50 (d, J=7.2 Hz, 3H).

1. concentrationthen concentrated under reduced pressure
2. washThe organic solution was washed with saturated NaHCO3 (20 mL), water (20 mL)
3. dry with materialdried over Na2SO4
4. customThe solvent was removed in vacuo
5. customto yield a brown oily residue
6. customThe oil was purified

ORD record

ord-bb777a8020364383a90616504a184ed2

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012461B2