Water → 3-Methoxy-4-pyridin-2-ylbenzaldehyde

HRID 2213099Notes

Reaction equation

HRID 2213099 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[C:6]#N.[H-].[OH2:18]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[CH:6]=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 166653HydrideHCID 21956523HCID 21956523, compound

Product 1

HCID 219565123-Methoxy-4-pyridin-2-ylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 3-methyoxy-4-pyridin-2-ylbenzonitrile (600 mg, 2.64 mmol) in CH2Cl2 (10 mL) was cooled to −78° C. and was treated with diisobutylalumnium hydride (3.2 mL of 1M in CH2Cl2, 3.2 mmol). After stirring the reaction mixture at −78° C. for 2 h, the temperature was raised to −40° C. before quenching the reaction with a mixture of silica gel (6 g) and water (2 mL) and then warmed to rt. The reaction mixture was dried (K2CO3 and MgSO4), and concentrated. The residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:4 to 1:1) to afford 3-methoxy-4-pyridin-2-ylbenzaldehyde.

Workup

  1. temperaturethe temperature was raised to −40° C.
  2. custombefore quenching
  3. customthe reaction
  4. temperaturewarmed to rt
  5. dry with materialThe reaction mixture was dried (K2CO3 and MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:4 to 1:1)

Sources & evidence

ORD record
ord-9774da904bc6423caac1cb8d54730f50
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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