Diisobutylaluminum hydride → (5,6-Dimethylpyridin-3-yl)methanol

HRID 420730Notes

Reaction equation

HRID 420730 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9](OC)=[O:10])[CH:5]=[N:6][C:7]=1[CH3:8].CC(C[AlH]CC(C)C)C.C(C(C(C([O-])=O)O)O)([O-])=O>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[N:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 38061142,3-DihydroxybutanedioateHCID 580017543-Pyridinecarboxylic acid, 5,6-dimethyl-, methyl ester

Product 1

HCID 46781823(5,6-Dimethylpyridin-3-yl)methanolYield 45.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 5,6-dimethyl-3-pyridinecarboxylate (276 mg, 1.671 mmol) in DCM (6 ml), DIBAL-H (1.5 M solution in toluene, 3.34 ml, 5.01 mmol) was added dropwise at −78° C. under N2. The reaction mixture was allowed to warm to rt and stirred overnight. To this solution was added saturated, aqueous NaK-tartrate solution followed by DCM. The organic phase was separated, dried and concentrated to afford 175 mg of the crude material. Purification by flash chromatography using Flashmaster II, a 5 g silica gel cartridge, and mixtures of DCM/MeOH as eluent afforded 105 mg of desired compound.

Workup

  1. additionTo this solution was added saturated
  2. customThe organic phase was separated
  3. customdried
  4. concentrationconcentrated
  5. customto afford 175 mg of the crude material
  6. customPurification by flash chromatography

Sources & evidence

ORD record
ord-0f3b0b51c08b4e67992b9ddf9aaabe61
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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