Water → (6-Methylpyridin-3-yl)methanol

HRID 868339Notes

Reaction equation

HRID 868339 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:18]=[CH:17][C:11]([C:12](OCC)=[O:13])=[CH:10][N:9]=1.O>C(OCC)C>[OH:13][CH2:12][C:11]1[CH:17]=[CH:18][C:8]([CH3:7])=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 281994Ethyl 6-methylnicotinateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 11228788(6-Methylpyridin-3-yl)methanolYield 80.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 11.4 g of lithium aluminum hydride in 500 ml of dry diethyl ether, 32.7 g of ethyl 6-methylnicotinate in 250 ml of dry diethyl ether is added dropwise at room temperature, and the mixture is refluxed for 1.5 hours. The reaction mixture is cooled to 0° C., and the remaining lithium aluminum hydride is decomposed by the cautious addition of 60 ml of water. The ether layer is decanted, and the residual solid is extracted with three 150-ml portions of diethyl ether. The combined extracts are dried over potassium carbonate and concentrated to give 19.6 g of crude 5-hydroxymethyl-2-methylpyridine.

Workup

  1. additionis added dropwise at room temperature
  2. temperaturethe mixture is refluxed for 1.5 hours
  3. customThe ether layer is decanted
  4. extractionthe residual solid is extracted with three 150-ml portions of diethyl ether
  5. dry with materialThe combined extracts are dried over potassium carbonate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a207923c88b1460b814fb374ece9c4c5
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

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