HCID 19361744, compound → 6-(Difluoromethyl)pyridine-2-carbaldehyde

HRID 931118Notes

Reaction equation

HRID 931118 reaction equation
[F:1][CH:2]([F:14])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]2OCC[O:10]2)[N:4]=1>C(O)=O>[F:14][CH:2]([F:1])[C:3]1[N:4]=[C:5]([CH:9]=[O:10])[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 19361744HCID 19361744, compound

Product 1

HCID 193617386-(Difluoromethyl)pyridine-2-carbaldehydeYield 53%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(difluoromethyl)-6-(1,3-dioxolan-2-yl)pyridine (0.5 g, 2.4 mmol) was added 85% formic acid (5 mL). The reaction mixture was warmed to 60° C. for 1.5 h. The mixture was then concentrated under reduced pressure, diluted with ice cold water, neutralized with aqueous sodium hydroxide (4N) and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, concentrated and purified via flash chromatography to afford 6-(difluoromethyl)picolinaldehyde (0.2 g, 51%). MS (ES+) (M+H) 158.16; LCMS retention time: 5.28 min (Method H).

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. additiondiluted with ice cold water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified via flash chromatography

Sources & evidence

ORD record
ord-1dfdb24863834208920af87fd042894b
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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