Water → Pyridine-2,3-dimethanol

HRID 964536

Reaction equation

HRID 964536 reaction equation
C[O:2][C:3]([C:5]1[C:10]([C:11](OC)=[O:12])=[CH:9][CH:8]=[CH:7][N:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[OH:2][CH2:3][C:5]1[C:10]([CH2:11][OH:12])=[CH:9][CH:8]=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 690582,3-Dimethyl 2,3-pyridinedicarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 12758260Pyridine-2,3-dimethanolYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution prepared by dissolving 29.5 g, of 2,3-dimethoxycarbonylpyridine in 200 ml of ethylether was added dropwise to a solution prepared by suspending 10 g of lithium aluminum hydride in 300 ml of dried ethylether at 0° C. This mixed solution was stirred at 20° C. for 3 hours and 30 ml of water was slowly added thereto at 0° C. The resulting solution was stirred for 5 hours at the room temperature and solid was filtered through celite. The filtrate was evaporated under reduced pressure and then the residual product was purified by a silica gel column chromatography (chloroform : methanol (10:1)) to give 10.4 g of the above title compound (yield: 75%).

Workup

  1. customA solution prepared
  2. dissolutionby dissolving 29.5 g
  3. customprepared
  4. customat 0° C
  5. customat 0° C
  6. stirringThe resulting solution was stirred for 5 hours at the room temperature and solid
  7. filtrationwas filtered through celite
  8. customThe filtrate was evaporated under reduced pressure
  9. customthe residual product was purified by a silica gel column chromatography (chloroform : methanol (10:1))

Sources & evidence

ORD record
ord-eeeb06389fab407c8661bc1ee5fd61a5
Source dataset
uspto-grants-1998_06
Patent number
US05770597

Linked notes

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