tert-Butoxy bis(dimethylamino)methane → 6-Fluoropyridine-2-carboxaldehyde

HRID 376274Notes

Reaction equation

HRID 376274 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.C([O:13]C(N(C)C)N(C)C)(C)(C)C.I([O-])(=O)(=O)=O.[Na+]>O1CCCC1>[F:1][C:2]1[N:3]=[C:4]([CH:8]=[O:13])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 960902-Fluoro-6-methylpyridineHCID 23667635Sodium periodate

Product 1

HCID 106067416-Fluoropyridine-2-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
140 °C

Procedure

30 g of 2-fluoro-6-methylpyridine (270 mmol) and 70 g of tert-butoxybis(dimethylamino)methane (405 mmol) are mixed under a nitrogen atmosphere. The mixture is heated at 140° C. for 24 hours. The mixture is diluted with 50 ml of tetrahydrofuran and the solution obtained is added dropwise to an aqueous solution of 115 g of sodium periodate (538 mmol). The mixture is stirred overnight at room temperature, the precipitate formed is removed by filtration and then the tetrahydrofuran is evaporated off. The residue is extracted with dichloromethane, the organic phase is dried over magnesium sulfate, filtered and then the solvent is evaporated under vacuum. The title product is isolated by distillation in a bulb oven, b.p.77 : 70-80° C. 34 g of a yellow oil containing about 20% of N,N-dimethylformamide are recovered.

Workup

  1. customthe solution obtained
  2. customthe precipitate formed
  3. customis removed by filtration
  4. customthe tetrahydrofuran is evaporated off
  5. extractionThe residue is extracted with dichloromethane
  6. dry with materialthe organic phase is dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-d00bb7af4eb04a89a2eccd57ae0bccfe
Source dataset
uspto-grants-2000_02
Patent number
US06020345

Reaction notes

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