Triethylamine → 2-(6-Chloropyridin-3-yl)ethan-1-ol

To a stirred solution of 2-chloropyridine-5-acetic acid (800 mg, 4.60 mmol) in THF (30 mL) at 0° C. under a nitrogen atmosphere was added triethylamine (2.20 mL, 10.3 mmol) and isobutyl chloroformate (1.20 mL, 9.33 mmol). The reaction was stirred for 50 minutes then sodium borohydride (1.77 g, 46 mmol) was added and the suspension stirred at r.t. for 16 h then at reflux for a further 4 h. The resulting mixture was partitioned between DCM (50 mL) and water (50 mL). The organic fraction was washed with brine (50 mL), dried (MgSO4) and concentrated in vacuo to yield the title compound (800 mg, quantitative) as a brown oil. LCMS (ES+) 158.0 (M+H)+, RT 1.81 minutes (85% purity) (Method 1).

1. stirringthe suspension stirred at r.t. for 16 h
2. temperatureat reflux for a further 4 h
3. customThe resulting mixture was partitioned between DCM (50 mL) and water (50 mL)
4. washThe organic fraction was washed with brine (50 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo

ORD record

ord-bfc67cf8fb004e7fb6bc63fe35a030db

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242116B2