Pivalic acid → 6-tert-Butyl-3-formylpyridine

HRID 1961436Notes

Reaction equation

HRID 1961436 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.[C:9](O)(=O)[C:10](C)([CH3:12])[CH3:11].S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+].[NH4+].[OH-]>OS(O)(=O)=O.O.[N+]([O-])([O-])=O.[Ag+]>[C:10]([C:6]1[CH:5]=[CH:4][C:3]([CH:7]=[O:8])=[CH:2][N:1]=1)([CH3:12])([CH3:11])[CH3:9]

Participants

8

Reactant 4

HCID 6417Pivalic acidHCID 75103-PyridinemethanolHCID 14923Ammonium HydroxideHCID 62648Ammonium Persulfate

Product 1

HCID 112406656-tert-Butyl-3-formylpyridineYield 43%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

3-Pyridinemethanol (2.2 g, 20.2 mmol), pivalic acid (10.3 g, 100.8 mmol) and silver nitrate (0.68, 4.0 mmol) were suspended in 10% aqueous H2SO4 (20 ml). Ammonium persulfate (9.2 g, 40.3 mmol) in H2O (40 ml) was added to the mixture. The mixture was stirred at r.t. for 2.0 h. NH4OH was added until pH=9. The product was extracted with EtOAc. The combined organic extracts were washed with water, dried (MgSO4), filtered and concentrated. Purification was done by flash chromatography (Pet. Ether/EtOAc 70:30) to give the title substance in 43% yield.

Workup

  1. extractionThe product was extracted with EtOAc
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. customto give the title substance in 43% yield

Sources & evidence

ORD record
ord-c84172b1e8fa4bd5bac7fa561882a1b8
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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