ethyl 4-(hydroxyMethyl)picolinate synthesis

6synthesis methods

Product Name:ethyl 4-(hydroxyMethyl)picolinate
CAS Number:59663-96-6
Molecular formula:C9H11NO3
Molecular Weight:181.19

64-17-5 Synthesis

64-17-5
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71935-32-5 Synthesis

71935-32-5
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59663-96-6
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Yield:59663-96-6 16%

Reaction Conditions:

Stage #1: ethanol;2-Cyano-4-(hydroxymethyl)pyridinewith chloro-trimethyl-silane at 50; for 12 h;
Stage #2: with water;sodium carbonate

Steps:

12 2-Ethoxycarbonylpyridine-4-methanol (Reference compound No.12-1)

Reference Example 12 2-Ethoxycarbonylpyridine-4-methanol (Reference compound No.12-1) Trimethylsilyl chloride (0.4 mL, 3.0 mmol) was added to a solution of 2-cyanopyridine-4-methanol (200 mg, 1.5 mmol, Reference compound No.11-1) in ethanol (3 mL) at 50°C under a nitrogen atmosphere, then the mixture was stirred for 12 hours. The mixture was allowed to stand, and a little water and sodium carbonate (160 mg, 1.5 mmol) were added thereto. The solution was dried over anhydrous magnesium sulfate, then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 43 mg of the title reference compound as a white solid. (Yield 16%) ¹H-NMR(500MHz,DMSO-d₆) δ 1.33(t,J = 7.0 Hz,3H),4.35(q,J = 7.0 Hz,2H),4.62(d,J = 5.8 Hz,2H),5.56(t,J = 5.8 Hz,1H),7.55(m,1H),8.01(dd,J = 1.6,0.6 Hz,1H),8.63(dd,J = 4.6, 0.6 Hz,1H)

References:

EP1602647,2005,A1 Location in patent:Page/Page column 53

586-95-8 Synthesis