* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With sodium borohydrid; acetic acid In tetrahydrofuran; methanol
Example 5 4-chloro-3-hydroxymethylpyridine To a solution of 4-chloro-3-pyridyl carboxyaldehyde (140 mg, 1.0 mmol) in THF (1 mL) at 0° C. was added methanol (1 mL) followed by portionwise addition of sodium borohydride (75 mg, 2.0 mmol). After 1 hr, acetic acid (0.15 ml) was added and the reaction mixture was evaporated to dryness with rotary evaporator at room temperature. The solid residue was chromatographed on silica gel column (1percent MeOH/dichloromethane) to afford 60 mg (42percent) of the title compound. 1H NMR (CDCl3) δ4.30 (br s, 1H), 4.80 (s, 2H), 7.30 (d, 1H, J=5), 8.34 (d, 1H, J=5), 8.62 (s, 1H).
42%
With sodium borohydrid; acetic acid In tetrahydrofuran; methanol
Example 5 4-chloro-3-hydroxymethylpyridine To a solution of 4-chloro-3-pyridyl carboxyaldehyde (140 mg, 1.0 mmol) in THF (1 mL) at 0° C. was added methanol (1mL) followed by portionwise addition of sodium borohydride (75 mg, 2.0 mmol). After 1 hr, acetic acid (0.15 ml) was added and the reaction mixture was evaporated to dryness with rotary evaporator at room temperature. The solid residue was chromatographed on silica gel column (1percent MeOH/dichloromethane) to afford 60 mg (42percent) of the title compound. 1H NMR (CDCl3) δ4.30 (br s, 1H), 4.80 (s, 2H), 7.30 (d, 1H, J=5), 8.34 (d, 1H, J=5), 8.62 (s, 1H).
42%
With sodium borohydrid; acetic acid In tetrahydrofuran; methanol
Example 5 4-chloro-3-hydroxymethylpyridine To a solution of 4-chloro-3-pyridyl carboxyaldehyde (140 mg, 1.0 mmol) in THF (1 mL) at 0° C. was added methanol (1 mL) followed by portionwise addition of sodium borohydride (75 mg, 2.0 mmol). After 1 hr, acetic acid (0.15 ml) was added and the reaction mixture was evaporated to dryness with rotary evaporator at room temperature. The solid residue was chromatographed on silica gel column (1percent MeOH/dichloromethane) to afford 60 mg (42percent) of the title compound. 1H NMR (CDCl3) δ 4.30 (br s, 1H), 4.80 (s, 2H), 7.30 (d, 1H, J=5), 8.34 (d, 1H, J=5), 8.62 (s, 1H).
42 %
With sodium borohydrid; acetic acid In tetrahydrofuran; methanol
Example 5 4-chloro-3-hydroxymethylpyridine To a solution of 4-chloro-3-pyridyl carboxyaldehyde (140 mg, 1.0 mmol) in THF (1 mL) at 0 °C was added methanol (1mL) followed by portionwise addition of sodium borohydride (75 mg, 2.0 mmol). After 1 hr, acetic acid (0.15 ml) was added and the reaction mixture was evaporated to dryness with rotary evaporator at room temperature. The solid residue was chromatographed on silica gel column (1percent MeOH / dichloromethane) to afford 60 mg (42 percent) of the title compound. 1H NMR (CDCl3) δ 4.30 (br s, 1H), 4.80 (s, 2H), 7.30 (d, 1H, J=5), 8.34 (d, 1H, J=5), 8.62 (s, 1H).
Reference：
[1] Synthesis, 1999, # 8, p. 1294 - 1296
[2] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 20, p. 5841 - 5863
[3] Tetrahedron, 2006, vol. 62, # 10, p. 2240 - 2246
[4] Journal of Medicinal Chemistry, 2002, vol. 45, # 13, p. 2832 - 2840
[5] Patent: US6025352, 2000, A,
[6] Patent: US6030965, 2000, A,
[7] Patent: US6057312, 2000, A,
[8] Patent: US6066630, 2000, A,
[9] Patent: US6087355, 2000, A,
[10] Patent: US5859256, 1999, A,
[11] Patent: EP1059293, 2000, A1,
[12] Synlett, 2013, vol. 24, # 1, p. 49 - 52
[13] Organic and Biomolecular Chemistry, 2014, vol. 12, # 30, p. 5781 - 5788
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