Hydrochloric Acid → 1-(Pyridin-2-yl)propan-2-one

HRID 900433

Reaction equation

HRID 900433 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].C([Li])CCC.[CH3:13][C:14](N(C)C)=[O:15].Cl>O1CCCC1.CCCCCC.C(OCC)(=O)C.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:14](=[O:15])[CH3:13]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 79752-MethylpyridineHCID 31374DimethylacetamideHCID 178418339Butyllithium

Product 1

HCID 959101-(Pyridin-2-yl)propan-2-one

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-75 °C

Procedure

2-Picoline (2 g) was dissolved in tetrahydrofuran (30 ml) and the solution was cooled to −75° C. Butyl lithium (14.73 ml. of a 1.6M-solution in hexane) was added dropwise and the mixture stirred for 2 h. Dimethylacetamide (1.87 ml) was then added dropwise and the reaction was allowed to warm up to room temperature and stirring was continued for a further 2 h. Water (8.6 ml) and 36% hydrochloric acid (1.3 ml) were added and after stirring for another 30 minutes, ethyl acetate was added. The separated solvent phase was washed with brine and then dried (MgSO4). On evaporation an oil was obtained and used without further purification.

Workup

  1. temperatureto warm up to room temperature
  2. stirringstirring
  3. waitwas continued for a further 2 h
  4. stirringafter stirring for another 30 minutes
  5. washThe separated solvent phase was washed with brine
  6. dry with materialdried (MgSO4)
  7. customOn evaporation an oil
  8. customwas obtained
  9. customused without further purification

Sources & evidence

ORD record
ord-c860e9ab15ed44159a48e3e704908253
Source dataset
uspto-grants-2008_04
Patent number
US07358376B2

Linked notes

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