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

HRID 862060
Notes
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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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 197015562-(5-Bromo-alpha-cyano-2-methoxymethoxybenzyl)-3-methoxymethoxypyridine

Product 1

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

Reagents, catalysts & solvents 2

HCID 94433
Tetrabutylammonium hydrogen sulfate
Catalyst
HCID 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05716971

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes