Water → HCID 131722549, compound

HRID 1976534Notes

Reaction equation

HRID 1976534 reaction equation
[Cl-].C[O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[O-].[Na+].[CH2:27]([O:29][N:30]=[C:31]([CH3:48])[C:32](=[N:34][O:35][C:36]1[C:41]([C:42](=O)[C:43]([O:45][CH3:46])=[O:44])=[CH:40][CH:39]=[CH:38][N:37]=1)[CH3:33])[CH3:28].O.[CH3:50][N:51](C)C=O>>[CH3:4][O:3][N:51]=[C:50]=[C:42]([C:41]1[C:36]([O:35][N:34]=[C:32]([CH3:33])[C:31](=[N:30][O:29][CH2:27][CH3:28])[CH3:48])=[N:37][CH:38]=[CH:39][CH:40]=1)[C:43]([O:45][CH3:46])=[O:44]

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 10942334Sodium MethoxideHCID 85362058HCID 85362058, compound

Product 1

HCID 131722549HCID 131722549, compound

Procedure

A mixture of 650 mg (1.9 mmol) of methoxymethyltriphenyl-phosphonium chloride and 340 g (1.9 mmol) of sodium methoxide solution (30% strength in methanol) in 8 ml of dimethylformamide was stirred for 10 minutes at room temperature. The reaction mixture was subsequently treated with 400 mg (0.95 mmol) of methyl [2-(2-ethoxyimino-1-methylpropylideneaminooxy)pyridin-3-yl]glyoxylate, dissolved in 4 ml of dimethylformamide. The reaction mixture was stirred for 4 hours at room temperature, hydrolyzed with 20 ml of water, and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. This gave 120 mg (38%) of the title compound as a yellow oil.

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-11db34054b544addb4ae6f18c6f5b913
Source dataset
uspto-grants-2001_05
Patent number
US06228810B1

Reaction notes

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