Methoxymethyl-triphenylphosphonium chloride → HCID 53931889, compound

HRID 843972Notes

Reaction equation

HRID 843972 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[O-].[Na+].[Cl:27][C:28]1[C:29]([CH3:40])=[C:30]([C:34](=O)[C:35]([O:37][CH3:38])=[O:36])[CH:31]=[CH:32][CH:33]=1>CN(C)C=O>[Cl:27][C:28]1[C:29]([CH3:40])=[C:30]([C:34](=[CH:2][O:3][CH3:4])[C:35]([O:37][CH3:38])=[O:36])[CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 10942334Sodium MethoxideHCID 22612678HCID 22612678, compound

Product 1

HCID 53931889HCID 53931889, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

92.3 g of methoxymethyltriphenylphosphonium chloride were suspended in 500 ml of anhydrous dimethylformamide, and 42.3 g of 30% strength sodium methanolate solution were added. After 20 minutes, a solution of 30 g of methyl 3-chloro-2-methylphenylglyoxylate in 200 ml of dimethylformamide was added dropwise to the pale yellow suspension. After a further 3 hours at room temperature, the mixture was poured into ice-water and extracted three times using methyl tert-butyl ether. It was dried over sodium sulfate, concentrated, and the crude product was applied to 100 g of silica gel. The product was eluted through a silica gel column using methyl tert-butyl ether. This gave 29 g of a colorless solid.

Workup

  1. waitAfter a further 3 hours at room temperature
  2. extractionextracted three times
  3. dry with materialIt was dried over sodium sulfate
  4. concentrationconcentrated
  5. washThe product was eluted through a silica gel column

Sources & evidence

ORD record
ord-919b2ea5ef7a479d9ecf0823ef499fa2
Source dataset
uspto-grants-2002_04
Patent number
US06380231B1

Reaction notes

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