Dimethylformamide → 2-(5-Bromo-2-methoxymethoxybenzoyl)-3-methoxymethoxypyridine

HRID 862060Notes

Reaction equation

HRID 862060 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH2:22][O:23][CH3:24])=[C:6]([CH:20]=1)[CH:7]([C:10]1[C:15]([O:16][CH2:17][O:18][CH3:19])=[CH:14][CH:13]=[CH:12][N:11]=1)C#N.C(=O)([O-])[O-:26].[K+].[K+].CN(C=O)C>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH2:22][O:23][CH3:24])=[C:6]([CH:20]=1)[C:7]([C:10]1[C:15]([O:16][CH2:17][O:18][CH3:19])=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:26]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 19701556α-[5-Bromo-2-(methoxymethoxy)phenyl]-3-(methoxymethoxy)-2-pyridineacetonitrile

Product 1

HCID 197015972-(5-Bromo-2-methoxymethoxybenzoyl)-3-methoxymethoxypyridineYield 87%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-(5-bromo-α-cyano-2-methoxymethoxybenzyl)-3-methoxymethoxypyridine (2.40 g), potassium carbonate (2.53 g), tetrabutylammonium hydrogensulfate (0.41 g) and DMF (24 ml) was stirred for 38 hours at room temperature. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The extract solution was washed with water, dried (anhydrous sodium sulfate), and concentrated to leave an oily product. The oily product was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane) to give 2-(5-bromo-2-methoxymethoxybenzoyl)-3-methoxymethoxypyridine (2.03 g) as an oily product, whose spectrum data are shown below.

Workup

  1. extractionwas subjected to extraction with ethyl acetate
  2. washThe extract solution was washed with water
  3. dry with materialdried (anhydrous sodium sulfate)
  4. concentrationconcentrated
  5. customto leave an oily product
  6. customThe oily product was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9dcf10af980d404bb991297834703957
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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