Potassium Carbonate → HCID 59865122, compound

HRID 221349Notes

Reaction equation

HRID 221349 reaction equation
C([O-])([O-])=O.[K+].[K+].C([O:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20]#[N:21])[CH:15]=1)(=O)C>O.CO>[OH:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20]#[N:21])[CH:15]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 15928279HCID 15928279, compound

Product 1

HCID 59865122HCID 59865122, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of K2CO3 (1.67 g, 12.1 mmol) in H2O (30 ml) was added to a stirred solution of 3-(2-cyanopyridin-4-yl)propyl acetate (4.94 g, 24.2 mmol) in MeOH (130 ml). After 25 min, the MeOH was removed under reduced pressure, then the aqueous phase was extracted three times with EtOAc. The combined organic extracts were dried (MgSO4), filtered, and concentrated to give a residue that was purified by column chromatography (IH-EtOAc, 1:3) to furnish 4-(3-hydroxypropyl)pyridine-2-carbonitrile: m/z (ES+)=163.1 [M+H]+. A solution of this alcohol (500 mg, 3.1 mmol) in DMF (20 ml) was treated with PDC (7 g, 18.6 mmol) and H2O (0.5 ml). The reaction was stirred for 16 h, before being partitioned between H2O and EtOAc. The aqueous phase was extracted twice with EtOAc, then the combined organic extracts were washed with brine, before being dried (MgSO4), filtered, and concentrated to give the title compound: m/z (ES−)=177.0 [M+H]+.

Workup

  1. customthe MeOH was removed under reduced pressure
  2. extractionthe aqueous phase was extracted three times with EtOAc
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue that
  7. customwas purified by column chromatography (IH-EtOAc, 1:3)

Sources & evidence

ORD record
ord-7a78b99d4e5b4f338c930fc50415e320
Source dataset
uspto-grants-2012_06
Patent number
US08207147B2

Reaction notes

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