Acetone → HCID 66607448, compound

HRID 1401241Notes

Reaction equation

HRID 1401241 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:9])=[CH:4][N:3]=1.C([Li])CCC.[CH3:15][C:16]([CH3:18])=[O:17]>C1(C)C=CC=CC=1>[Br:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([C:16]([OH:17])([CH3:18])[CH3:15])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 27344292,5-Dibromo-4-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 66607448HCID 66607448, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

2,5-Dibromo-4-methylpyridine (4.0 g, 15.94 mmol) was dissolved in toluene (60.0 mL) and the reaction was cooled to −78° C. Butyllithium (7.01 mL, 17.54 mmol) was added dropwise and the reaction was allowed to stir for 30 min. Acetone (4.69 mL, 63.8 mmol) was then added and the reaction was allowed to warm to rt and stir for 16 h. The reaction was quenched with saturated ammonium chloride, extracted into ethyl acetate (3×200 mL) and washed with water followed by brine. The organics were dried over magnesium sulfate and volatiles removed under reduced pressure. The compound was purified on silica gel chromatography (0-50% ethyl acetate in hexanes) to afford 2-(5-bromo-4-methylpyridin-2-yl)propan-2-ol (2.33 g, 10.13 mmol, 63.5% yield). MS (ESI) m/z 230.3 [M]+, 232.3 [M+2]+.

Workup

  1. temperatureto warm to rt
  2. stirringstir for 16 h
  3. customThe reaction was quenched with saturated ammonium chloride
  4. extractionextracted into ethyl acetate (3×200 mL)
  5. washwashed with water
  6. dry with materialThe organics were dried over magnesium sulfate and volatiles
  7. customremoved under reduced pressure
  8. customThe compound was purified on silica gel chromatography (0-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-74369c7a94224acc9d316b1937b331e6
Source dataset
uspto-grants-2014_12
Patent number
US08907087B2

Reaction notes

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