Tetrahydrofuran → (6-Chloropyridin-2-yl)methanol
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O1CCCC1.[Cl:6][C:7]1[N:12]=[C:11]([C:13](O)=[O:14])[CH:10]=[CH:9][CH:8]=1.O1CCCC1.B.[OH-].[Na+]>O>[Cl:6][C:7]1[N:12]=[C:11]([CH2:13][OH:14])[CH:10]=[CH:9][CH:8]=1O1CCCC1.[Cl:6][C:7]1[N:12]=[C:11]([C:13](O)=[O:14])[CH:10]=[CH:9][CH:8]=1.O1CCCC1.B.[OH-].[Na+]>O>[Cl:6][C:7]1[N:12]=[C:11]([CH2:13][OH:14])[CH:10]=[CH:9][CH:8]=1A dry flask was charged with 25 mL of anhydrous tetrahydrofuran and 6-chloropyridine-2-carboxylic acid (2.00 g, 12.69 mmol) and then cooled to 10° C. This was treated dropwise with tetrahydrofuran-borane (1.0 M solution in THF, 38.1 mL) over 10 minutes under nitrogen. This was stirred with cooling for 15 minutes, then at ambient temperature for 4 h. The reaction was then cooled to 0° C., and 10 mL of water were added slowly. The resultant mixture was poured into 50 mL of 1 M aqueous sodium hydroxide and extracted 2×75 mL of ethyl acetate. The organic extracts were combined and washed with brine, then dried over sodium sulfate and filtered. Concentration in vacuo yielded 589.1 mg of a white solid as the title compound (I-5a).
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