Diisobutylaluminum hydride → (5-Bromo-6-methylpyridin-3-yl)methanol

HRID 420723Notes

Reaction equation

HRID 420723 reaction equation
[Br: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>[Br: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 58001778Methyl 5-bromo-6-methylnicotinate

Product 1

HCID 58001752(5-Bromo-6-methylpyridin-3-yl)methanolYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 5-bromo-6-methyl-3-pyridinecarboxylate (76 mg, 0.330 mmol) in DCM (1.5 ml), DIBAL-H (1.5 M solution in toluene, 0.661 ml, 0.991 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 56 mg of (5-bromo-6-methyl-3-pyridinyl)methanol (56 mg, 84%) pure enough to be used in the next step.

Workup

  1. additionTo this solution was added saturated
  2. customThe organic phase was separated
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-61123e0608194a738edfa6a8bde78289
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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