Water → HCID 57954383, compound

HRID 221350Notes

Reaction equation

HRID 221350 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[CH:6]=1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-:25][Cr](O[Cr]([O-])(=O)=O)(=O)=O.O>CN(C=O)C>[C:11]([C:7]1[CH:6]=[C:5]([CH2:4][CH2:3][C:2]([OH:25])=[O:1])[CH:10]=[CH:9][N:8]=1)#[N:12]

Participants

5

Reactant 3

HCID 962WaterHCID 2724130Cornforth reagentHCID 59865122HCID 59865122, compound

Product 1

HCID 57954383HCID 57954383, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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. custombefore being partitioned between H2O and EtOAc
  2. extractionThe aqueous phase was extracted twice with EtOAc
  3. washthe combined organic extracts were washed with brine
  4. dry with materialbefore being dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d9b1539003394992a6b8ccc453fc20a9
Source dataset
uspto-grants-2012_06
Patent number
US08207147B2

Reaction notes

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