Trifluoroacetic acid → HCID 59570065, compound

HRID 2071097Notes

Reaction equation

HRID 2071097 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:5]=[N:6][CH:7]=[C:8]([C:10]([CH3:12])=[CH2:11])[CH:9]=1.C(O)(C(F)(F)F)=O>>[CH2:11]=[C:10]([C:8]1[CH:7]=[N:6][CH:5]=[C:4]([CH:9]=1)[CH:3]=[O:2])[CH3:12]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68670854HCID 68670854, compound

Product 1

HCID 59570065HCID 59570065, compound

Procedure

To 3-(dimethoxymethyl)-5-(prop-1-en-2-yl)pyridine (2.2 g, 11.3 mmol), TFA (5.2 ml, 67.8 mmol) was added at 0° C., and the reaction mixture was stirred at rt for 16 h. Then volatiles were removed under vacuum and the reaction mixture was diluted with ether. Ether layer was washed with aqueous sodium bicarbonate solution, water, brine and dried. The organic layer was dried and evaporated to provide 5-(prop-1-en-2-yl)nicotinaldehyde.

Workup

  1. customThen volatiles were removed under vacuum
  2. additionthe reaction mixture was diluted with ether
  3. washEther layer was washed with aqueous sodium bicarbonate solution, water, brine
  4. customdried
  5. customThe organic layer was dried
  6. customevaporated

Sources & evidence

ORD record
ord-caa0c31701574febac5e212632b9a65f
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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