Acetone → HCID 58268542, compound

HRID 1517565Notes

Reaction equation

HRID 1517565 reaction equation
C([N-]C(C)C)(C)C.[Li+].[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[CH3:16][C:17]([CH3:19])=[O:18]>O1CCCC1>[Br:9][C:10]1[C:15]([C:17]([OH:18])([CH3:19])[CH3:16])=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 79732-BromopyridineHCID 2724682Lithium diisopropylamide

Product 1

HCID 58268542HCID 58268542, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Lithium diisopropylamide (2M, 12.5 mL, 25 mmol) is dissolved in tetrahydrofuran (40 mL) and cooled to −78° C. 2-Bromopyridine (3.9 g, 25 mmol) is added dropwise and the reaction is stirred for 3 hr. before adding acetone (1 mL, dried over freshly activated molecular sieves) and allowing warming to room temperature. The reaction is quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layer is dried over magnesium sulfate and evaporated. The residue is purified by flash column chromatography on silica, eluting with 20% hexane/tert-butyl methyl ether to give the title compound (1.4 g, 26%). 1H-NMR (d6-dimethyl sulfoxide): 8.23 (dd, J=1.9, 4.5 Hz, 1H), 8.19 (dd, J=2.0, 7.8 Hz, 1H), 7.44 (dd, J=4.5, 7.7 Hz, 1H), 5.43 (s, 1H), 2.12 (s, 1H), 1.46 (s, 6H).

Workup

  1. customdried over freshly activated molecular sieves) and
  2. temperatureallowing warming to room temperature
  3. customThe reaction is quenched with saturated ammonium chloride
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. customevaporated
  7. customThe residue is purified by flash column chromatography on silica
  8. washeluting with 20% hexane/tert-butyl methyl ether

Sources & evidence

ORD record
ord-5560cda7ab494f47be8921b2a2256d92
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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