Trifluoroacetic anhydride → (3-Isopropylpyridin-2-YL)methanol

Participants

Reaction Steps

To a stirred solution of 3-isopropyl-2-methyl-pyridine 1-oxide (26.05 g, 173 mmol) in CH2Cl2 (690 mL) was added dropwise TFAA (51.83 mL) over 30 min. under N2 then stirred for an additional 3 h. Caution: exothermic reaction on addition of TFAA. The mixture was concentrated in vacuo to a minimum volume. Brine (200 mL) was added, basified to pH 9 with solid K2CO3 slowly, then the aqueous mixture was extracted with CH2Cl2 (3×100 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to afford (3-isopropyl-pyridin-2-yl)-methanol (26 g, 99%) as an orange oil. 1H NMR(CDCl3) δ 1.24 (d, 6H, 7.0 Hz), 2.92 (sep, 1H, J=6.6 Hz), 4.79 (s, 2H), 7.02-7.25 (m, 1H), 7.61 (d, 1H, J=7.9 Hz), 8.41 (d, 1H, J=4.8 Hz).

Provenance & Evidence