1-(2-Chloropyridin-3-yl)ethanol

Step 1 : l-(2-Chloropyridin-3-yl)ethanol.

Dry THF (400 mL) and n-butyllithium (1.6 M in hexane, 63 mL, 0.1 mol) were introduced into a IL flask under nitrogen at -70⁰C. A solution of dry diisopropylamine (10.1 g, 0.1 mol) in THF (25 mL) was added dropwise to the mixture at -70 ⁰C. The mixture was then kept for 1 h at 0 ⁰C and then cooled to -70 ⁰C. A solution of 2- chloropyridine (11.3 g, 0.1 mol) in THF (25 mL) was added dropwise to the mixture at - 70 ⁰C and the mixture was stirred for 3 h at this temperature. A solution of acetaldehyde (4.85 g, 0.11 mol) in dry THF (50 mL) was then added dropwise and the mixture was kept for 3 h at -70 ⁰C. A solution of water (4 mL) in THF (40 mL), acidified by a few drops of concentrated hydrochloric acid, was added to the mixture at -40 ⁰C and then water (200 mL) was introduced at -10 ⁰C. Extraction with diethyl ether (3x150 mL), drying over anhydrous sodium sulfate, and evaporation gave a crude product, which was purified by column chromatography to yield an oil (10 g, 64%). 
*1H NMR (CDCl₃) 8.15 (dd, J = 5 and 2 Hz, 1 H), 7.95 (dd, J = 8 and 2 Hz, 1 H), 7.20 (dd, J = 8 and 5 Hz, 1 H), 5.15 (d, J = 7 Hz, 1 H), 3.90 (s, 1 H), 1.45 (d, J = 7 Hz, 3 H).

* NMR values reported in Journal of Chemical Society Perkin Trans 1 : Organic and Bio-organic Chemistry, 1990, 9, 2409-2415.

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