Ethyl Acetate → 5-Chloro-2-(3-methoxypropyl)pyridine-4-carbaldehyde

HRID 561827Notes

Reaction equation

HRID 561827 reaction equation
[Cl:1][C:2]1[C:3]([CH:13](OC)[O:14]C)=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][O:11][CH3:12])=[N:6][CH:7]=1.CCOC(C)=O.[OH-].[Na+]>Cl>[Cl:1][C:2]1[C:3]([CH:13]=[O:14])=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][O:11][CH3:12])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 667628875-Chloro-4-(dimethoxymethyl)-2-(3-methoxypropyl)pyridine

Product 1

HCID 714237335-Chloro-2-(3-methoxypropyl)pyridine-4-carbaldehydeYield 99.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
80 °C

Procedure

5-Chloro-4-dimethoxymethyl-2-(3-methoxy-propyl)-pyridine (25.5 g, 98.2 mmol) was dissolved in aq. 1M HCl (500 mL), and the mixture was heated to 80° C. for 2 h. The mixture was allowed to cool to rt, and EtOAc was added. The mixture was cooled to 0° C., and was basified with an aq. 2.5M NaOH until a pH=10 was reached. The layers were separated, and the org. layer was dried over MgSO4, filtered, and concentrated under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (98.1 mmol, 99%) that was used further without purification. LC-MS: tR=0.62 min; ES+: 246.12.

Workup

  1. temperatureto cool to rt
  2. temperatureThe mixture was cooled to 0° C.
  3. customThe layers were separated
  4. dry with materiallayer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customDrying the residue under high vacuum

Sources & evidence

ORD record
ord-14394d12fbf9447fbc12ce1a6ba901e2
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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