Ethyl Acetate → Methyl 2-(2-ethynylpyridin-3-yl)acetate

Temperature

0 °C

A solution of TBAF (1 M solution in THF; 0.207 mL, 0.207 mmol) was added to a solution of methyl 2-(2-((triethylsilyl)ethynyl)pyridin-3-yl)acetate (I119) (50.0 mg, 0.173 mmol) in THF (2 mL) at 0° C. The reaction was stirred for 2 minutes at 0° C. then diluted with saturated NaHCO3 (20 mL). EtOAc (20 mL) was then added and the layers separated. The aqueous layer was extracted with EtOAc (2×20 mL) then the combined organic layers were washed with water 20 mL), brine (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 (0-55% EtOAc in cyclohexane) to afford the title compound (I120) (25.9 mg, 86%) as an orange oil; 1H NMR (400 MHz, CDCl3) δ 8.52 (dd, J=4.8, 1.6 Hz, 1H), 7.65 (dd, J=7.9, 1.6 Hz, 1H), 7.29-7.24 (m, peak obscured by solvent), 3.87 (s, 2H), 3.72 (s, 3H), 3.35 (s, 1H). LCMS Method C: rt 4.74 min; m/z 176 [M+H]+.

1. customthe layers separated
2. extractionThe aqueous layer was extracted with EtOAc (2×20 mL)
3. washthe combined organic layers were washed with water 20 mL), brine (20 mL)
4. dry with materialdried over Na2SO4
5. customThe solvent was removed in vacuo
6. customto yield a brown oily residue
7. customThe oil was purified

ORD record

ord-dae0f21f64ec4232ac85233bd3d2bc72

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012461B2