HCID 22008807, compound → HCID 22008839, compound

HRID 322002Notes

Reaction equation

HRID 322002 reaction equation
C([Li])CCC.Br[C:7]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:8]=1[C:9]([N:11]1[CH:16]=[CH:15][C:14](=[O:17])[CH2:13][CH2:12]1)=[O:10]>C1COCC1>[CH3:23][O:22][C:19]1[CH:18]=[C:8]2[C:7](=[CH:21][CH:20]=1)[CH:12]1[CH2:13][C:14](=[O:17])[CH2:15][CH2:16][N:11]1[C:9]2=[O:10]

Participants

4

Reactant 2

HCID 22008807HCID 22008807, compoundHCID 178418339Butyllithium

Product 1

HCID 22008839HCID 22008839, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Butyl lithium (3.1 ml, 0.9 M in hexanes, 2.8 mmol) was added dropwise to a solution of 1-(2-bromo-5-methoxybenzoyl)-2,3dihydro-4-pyridinone (0.75 g, 2.4 mmol) in THF (20 ml) at −78° C. After stirring for 2 h, the reaction was quenched with water, extracted with ethyl acetate, the extract dried over magnesium sulphate and evaporated. The residue was purified by flash column chromatography on silica eluting with 50% ethyl acetate in hexane to yield the title compound as a colourless oil (240 mg). MS (+EI) m/z 231 [M+].

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialthe extract dried over magnesium sulphate
  4. customevaporated
  5. customThe residue was purified by flash column chromatography on silica eluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-9f15eada97854b8e82e194fe84abc509
Source dataset
uspto-grants-2001_04
Patent number
US06211189B1

Reaction notes

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