Methyl 4-pyridin-3-ylbenzoate → 4-(Pyridin-3-yl)benzaldehyde

HRID 1603062Notes

Reaction equation

HRID 1603062 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([CH:3]=[O:2])=[CH:5][CH:6]=2)[CH:11]=1

Participants

4

Reactant 2

HCID 4133187Methyl 4-pyridin-3-ylbenzoateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 36930464-(Pyridin-3-yl)benzaldehydeYield 97.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-pyridin-3-yl-benzoic acid methyl ester (124 mg in 5.0 mL dry methylene chloride) at -78° C. was added 1.46 mL of a 1M solution of diisobutylaluminum hydride in methylene chloride and the mixture stirred at low temperature. After 2 hours, the reaction was quenched by the addition of acetone, warmed to room temperature and stirred for 20 minutes with 1.5 mL of a 1M solution of tartaric acid. At this time the mixture was extracted with methylene chloride and the combined organics dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (ethyl acetate:hexane, 1:1; then methylene chloride:methanol, 95:5) gave the title compound (104 mg).

Workup

  1. customthe reaction was quenched by the addition of acetone
  2. stirringstirred for 20 minutes with 1.5 mL of a 1M solution of tartaric acid
  3. extractionAt this time the mixture was extracted with methylene chloride
  4. dry with materialthe combined organics dried over sodium sulfate
  5. customPurification of the
  6. concentrationconcentrate by flash chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-1073716d1b6b409f86aa07a68cf84ca3
Source dataset
uspto-grants-1999_11
Patent number
US05985901

Reaction notes

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