Water → 2-(3,5-Dichloro-pyridin-4-yl)-1-(3,4-dimethoxy-phenyl)-ethanone

HRID 2076271Notes

Reaction equation

HRID 2076271 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].C([N-]C(C)C)(C)C.[Li+].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:23](Cl)=[O:24].O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[CH2:8][C:23]([C:22]1[CH:26]=[CH:27][C:28]([O:29][CH3:30])=[C:20]([O:19][CH3:18])[CH:21]=1)=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 77070Veratroyl chlorideHCID 2724682Lithium diisopropylamideHCID 109538273,5-Dichloro-4-methylpyridine

Product 1

HCID 668811982-(3,5-Dichloro-pyridin-4-yl)-1-(3,4-dimethoxy-phenyl)-ethanoneYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 3,5-dichloro-4-methyl-pyridine (2.06 g, 12.7 mmol) in dry tetrahydrofuran (30 ml) was cooled down to −78° C., then a 1.8 M solution of lithium diisopropylamide in tetrahydrofuran (7.4 ml, 13.3 mmol) was added dropwise under stirring, keeping the temperature below −70° C. The resulting solution was stirred for 30 min., then a solution of 3,4-dimethoxy-benzoyl chloride (2.55 g, 12.7 mmol) in dry tetrahydrofuran (20 ml) was added dropwise, maintaining the temperature below −70° C. After stirring for 15 minutes, ice (20 g) was added, followed by further 500 ml of water. The mixture was extracted with ethyl acetate (2×50 ml), the combined organic layers were dried over sodium sulphate and evaporated under reduced pressure to give an oil that was purified by flash chromatography (Eluent: ethyl acetate/petroleum ether from 10/90 to 30/70 v:v). 2.1 grams (6.4 mmol, 52% yield) of the title compound were obtained as a white solid.

Workup

  1. customthe temperature below −70° C
  2. stirringThe resulting solution was stirred for 30 min.
  3. temperaturemaintaining the temperature below −70° C
  4. stirringAfter stirring for 15 minutes
  5. extractionThe mixture was extracted with ethyl acetate (2×50 ml)
  6. dry with materialthe combined organic layers were dried over sodium sulphate
  7. customevaporated under reduced pressure
  8. customto give an oil that
  9. customwas purified by flash chromatography (Eluent: ethyl acetate/petroleum ether from 10/90 to 30/70 v:v)

Sources & evidence

ORD record
ord-8718936973e042a19e7f2cae99b59492
Source dataset
uspto-grants-2011_04
Patent number
US07923565B2

Reaction notes

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