3,3-Bis-(2-pyridyl)propionaldehyde dimethyl acetal → 3,3-Bis-(2-pyridyl)propionaldehyde

HRID 2181639Notes

Reaction equation

HRID 2181639 reaction equation
C[O:2][CH:3](OC)[CH2:4][CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1>Cl.ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>[N:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[CH2:4][CH:3]=[O:2]

Participants

5

Reactant 1

HCID 224820933,3-Bis-(2-pyridyl)propionaldehyde dimethyl acetal

Product 1

HCID 224821053,3-Bis-(2-pyridyl)propionaldehydeYield 75.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1.86 g of Compound 16A and 0.08 g of 1,4-dihydroquinone in 36 mL of 2 N HCl was stirred at 80° C. for 15 min, cooled to 0° C., diluted with 50 mL of dichloromethane and neutralized with 20% aq. sodium carbonate (pH=7-8). The organic layer was dried on sodium sulphate and evaporated to dryness affording 1.15 g of crude title compound as a grey glassy solid, which was used in the next step without any further purification.

Workup

  1. customThe organic layer was dried on sodium sulphate
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-035c63fa3b5e411fab22a54086da83ec
Source dataset
uspto-grants-2005_05
Patent number
US06894052B1

Reaction notes

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