Pivalaldehyde → HCID 22009516, compound

HRID 322030Notes

Reaction equation

HRID 322030 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([F:8])=[N:6][CH:7]=1.C([Li])CCC.CC(C)(C)[CH:17]=[O:18]>CCOCC>[F:8][C:5]1[N:6]=[CH:7][C:2]([CH2:17][OH:18])=[CH:3][C:4]=1[CH3:9]

Participants

5

Reactant 3

HCID 12417PivalaldehydeHCID 120569025-Bromo-2-fluoro-3-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 22009516HCID 22009516, compoundYield 103.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-70 °C

Procedure

5-Bromo-2-fluoro-3-methylpyridine (2.0 g, 0.011 mol) was dissolved with stirring in anhydrous ether (30 mL) and cooled to −70° C. This was treated at <−60° C. with n-butyl lithium (4.8 mL, 2.5M in hexane, 0.012 mol) and the reaction mixture stirred at <−70° C. for one hour. Trimethylacetaldehyde (1.14 g, 0.013 mol) was added and the reaction mixture allowed to warm to −10° C. The reaction mixture was quenched with ammonium chloride solution and extracted with ethyl acetate. The organic extract was washed with water and brine, dried (Na2SO4) and evaporated to dryness. Purification of the residue by chromatography over silica (5-25% ethyl acetate:hexane) gave the desired product (1.6 g, 77%) as a clear oil.

Workup

  1. temperatureto warm to −10° C
  2. customThe reaction mixture was quenched with ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated to dryness
  8. customPurification of the residue by chromatography over silica (5-25% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-33185891b54946c7a2bc831739e70285
Source dataset
uspto-grants-2001_04
Patent number
US06211202B1

Reaction notes

Loading…