Methyl bromoacetate → HCID 18369422, compound

HRID 1699770Notes

Reaction equation

HRID 1699770 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[O:9])=[CH:3][CH:2]=1.C([N-]C(C)C)(C)C.[Li+].Br[CH2:27][C:28]([O:30][CH3:31])=[O:29]>O1CCCC1.C1(C)C=CC=CC=1>[CH3:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([C:8](=[O:9])[CH:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 60984Methyl bromoacetateHCID 2724682Lithium diisopropylamideHCID 100824531-(4-Methoxyphenyl)-2-(pyridin-4-yl)ethan-1-one

Product 1

HCID 18369422HCID 18369422, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon, 2-(4-pyridyl)-4′-methoxyacetophenone (J. Am. Chem. Soc., 112, 2163-3168, 1990: Dimitrios Stefanidis and John W. Bunting; 9.6 g, 42.3 mmol) was suspended in tetrahydrofuran (200 ml), and under ice cooling, lithium diisopropylamide (2.0 M solution; 25 ml, 50.0 mmol) was added. At the same temperature, the mixture was stirred for 30 minutes. Methyl bromoacetate (6.0 ml, 63.4 mmol) was then added dropwise, and the mixture was stirred under ice cooling for 1 hour and then at room temperature for 2 hours. The reaction mixture was diluted with toluene. The mixture was washed successively with 2 N hydrochloric acid, water and a brine, and was then dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was separated and purified by chromatography on a silica gel column [silica gel: 100 g, hexane/ethyl acetate (1/2)], whereby the title compound (10.63 g, 84.1%) was obtained as a brown oil.

Workup

  1. stirringthe mixture was stirred under ice cooling for 1 hour
  2. waitat room temperature for 2 hours
  3. washThe mixture was washed successively with 2 N hydrochloric acid, water
  4. dry with materiala brine, and was then dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was separated
  7. custompurified by chromatography on a silica gel column [silica gel: 100 g, hexane/ethyl acetate (1/2)], whereby the title compound (10.63 g, 84.1%)
  8. customwas obtained as a brown oil

Sources & evidence

ORD record
ord-98138e12ebea4a45b98a5c8e4f2ad6a1
Source dataset
uspto-grants-2002_02
Patent number
US06348468B1

Reaction notes

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