Dimethylformamide → 6-tert-Butoxypyridine-2-carbaldehyde

HRID 564820Notes

Reaction equation

HRID 564820 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].BrC1C=CC=C([C:13]([CH3:16])([CH3:15])[CH3:14])N=1.C[N:18]([CH:20]=[O:21])C.C1C[O:25][CH2:24]C1>CCCCCC>[C:13]([O:21][C:20]1[CH:1]=[CH:2][CH:3]=[C:4]([CH:24]=[O:25])[N:18]=1)([CH3:14])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8028Tetrahydrofuran2×HCID 221134152-Bromo-6-tert-butylpyridineHCID 178418339Butyllithium

Product 1

HCID 27610086-tert-Butoxypyridine-2-carbaldehydeYield 93%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

“Butyl lithium (13.6 ml of a 2.5M solution in hexane) was added to a solution of 2-bromo-6-tert-butylpyridine (4.0 g) in THF (100 ml) at −90° C. This was stirred for 30 minutes then DMF (3 ml) in THF (15 ml) was added quickly. The reaction was allowed to reach room temperature then quenched with a saturated solution of ammonium chloride and extracted with ether. The combined organic extract was washed with brine, dried and concentrated to give 2-tert-butoxy-6-pyridine carboxaldehyde (2.8 g, 93% yield ) as a brown liquid; 1H NMR (270 MHz): δ 1.65(9H,s), 6.89(1H,s), 7.51(1H,d), 7.68(1H,t), 9.92(1H,s) ppm.

Workup

  1. customto reach room temperature
  2. customthen quenched with a saturated solution of ammonium chloride
  3. extractionextracted with ether
  4. extractionThe combined organic extract
  5. washwas washed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ed971c0ec57a4d8384b9f198f0c40112
Source dataset
uspto-grants-2001_01
Patent number
US06169101A

Reaction notes

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