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0 °C

Methyl 6-((tetrahydro-2H-pyran-2-yloxy)methyl)nicotinate (1.5 g, 6.0 mmol) was dissolved in THF (30 mL) and cooled to 0° C. under nitrogen. DIBAL-H (1.0 M in THF, 21 mL, 21 mmol) was added dropwise, via a syringe over 5 min, and stirred for 90 min. The reaction mixture was warmed to room temperature, and quenched with water (25 mL), followed by saturated NH4Cl (10 mL). After stirring for 10 minutes, the mixture was basified with solid KOH, extracted with CH2Cl2 (2×100 mL), washed with brine (100 mL), dried (MgSO4), filtered, and concentrated, to afford (6-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-3-yl)methanol as a yellow oil (1.3 g, 97%).

1. temperatureThe reaction mixture was warmed to room temperature
2. customquenched with water (25 mL)
3. stirringAfter stirring for 10 minutes
4. extractionextracted with CH2Cl2 (2×100 mL)
5. washwashed with brine (100 mL)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated