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

Temperatur

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). LCMS Method C: rt 5.92 min; m/z 189 [M+H]+.

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-Eintrag

ord-b6c58a3199ff47dbb47e3790b8eff951

Quelldatensatz

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09421205B2