Methyl 4-chlorobenzoate → 1-(4-Chlorophenyl)-2-(4-chloropyridin-2-yl)ethanone

HRID 932059Notes

Reaction equation

HRID 932059 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.[Cl:9][C:10]1[CH:19]=[CH:18][C:13]([C:14](OC)=[O:15])=[CH:12][CH:11]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[Cl:9][C:10]1[CH:19]=[CH:18][C:13]([C:14](=[O:15])[CH2:8][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][N:5]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 14307Methyl 4-chlorobenzoateHCID 5813924-Chloro-2-methylpyridineHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 585738901-(4-Chlorophenyl)-2-(4-chloropyridin-2-yl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-chloro-2-methylpyridine (23.07 g, 181 mmol) and methyl 4-chlorobenzoate (30.8 g, 181 mmol) in dry THF (500 mL) at 0° C. was added 1 M LiHMDS in THF (63.5 g, 380 mmol) slowly via a dropping funnel. When complete, the reaction was quenched with NaHCO3 solution, concentrated under reduced pressure, and extracted with ethyl acetate. The combined organics were dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure to provide the title compound.

Workup

  1. customWhen complete, the reaction was quenched with NaHCO3 solution
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-12b0d5304431498fa7a5da22646929d1
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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