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

HRID 420709Notes

Reaction equation

HRID 420709 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](OC)=[O:9])=[CH:4][C:3]=1[CH3:12].CC(C[AlH]CC(C)C)C>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[CH3:12]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 12404031Methyl 6-chloro-5-methylpyridine-3-carboxylate

Product 1

HCID 11686949(6-Chloro-5-methylpyridin-3-yl)methanolYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 6-chloro-5-methyl-3-pyridinecarboxylate (84 mg, 0.453 mmol) in DCM (2 ml), DIBAL-H (1.5 M solution in toluene, 0.905 ml, 1.358 mmol) was added dropwise under N2 at −78° C. The reaction mixture was allowed to attain rt and stirred overnight. After 18 h, TLC showed no starting material. The reaction was quenched by addition of sodium-potassium tartrate saturated solution, extracted with DCM, dried, filtered, and concentrated to afford (6-chloro-5-methyl-3-pyridinyl)methanol (63 mg, 0.400 mmol, 88% yield) pure enough to be used in the next step.

Workup

  1. customto attain rt
  2. waitAfter 18 h
  3. customThe reaction was quenched by addition of sodium-potassium tartrate saturated solution
  4. extractionextracted with DCM
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-897fb46fdb5f43529eb7c167b8c301fe
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

Loading…