Ethanol → Ethyl 6-(hydroxymethyl)pyridine-3-carboxylate

HRID 1612035Notes

Reaction equation

HRID 1612035 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([O-:9])=[O:8])[CH:4]=[CH:3][C:2]=1[C:10]([O:12]CC)=O.[BH4-].[Na+].[Cl-].[Ca+2].[Cl-].O.[CH2:21](O)[CH3:22]>>[OH:12][CH2:10][C:2]1[CH:3]=[CH:4][C:5]([C:7]([O:9][CH2:21][CH3:22])=[O:8])=[CH:6][N:1]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 425440302,5-Pyridinedicarboxylic acid, 2-ethyl ester

Product 1

HCID 15045504Ethyl 6-(hydroxymethyl)pyridine-3-carboxylateYield 84%

Conditions

Temperature
-5 °C

Procedure

45.77 g (205 mmol) of ethyl 2,5-pyridine-dicarboxylate was dissolved in 410 ml of absolute ethanol in a one-liter round-bottomed flask. The reaction medium was cooled to −5° C. and 5.04 g (133.2 mmol) of sodium borohydride was added, followed by portionwise addition of 14.79 g (133.2 mmol) of calcium chloride, while keeping the temperature below −5° C. The reaction medium was stirred at −5° C. for two hours and poured into water. The product was extracted with ethyl ether and washed with water and the organic phase was then dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a column of silica eluted with ethyl ether, in order to obtain 31.33 g (84%) of a white crystalline solid.

Workup

  1. customthe temperature below −5° C
  2. extractionThe product was extracted with ethyl ether
  3. washwashed with water
  4. dry with materialthe organic phase was then dried over magnesium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. customwas purified by chromatography on a column of silica
  8. washeluted with ethyl ether, in order

Sources & evidence

ORD record
ord-4db1771cc3784819856695f8385d42d5
Source dataset
uspto-grants-2006_01
Patent number
US06992095B2

Reaction notes

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