Water → HCID 23458381, compound

HRID 1679975Notes

Reaction equation

HRID 1679975 reaction equation
[OH:1][CH:2]([CH:8]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:25]I.[H-].[Na+].O>CN(C)C=O>[CH3:25][O:1][CH:2]([CH:8]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15572611HCID 15572611, compound

Product 1

HCID 23458381HCID 23458381, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
3 °C

Procedure

To 2 g of ethyl 2-hydroxy-3-phenyl-3-(2-nitro-phenoxy)-propionate dissolved in 30 ml of anhydrous dimethylformamide, CH3I (0.78 ml) was added at 3° C., then, in two additions, at the same temperature, NaH 50% (0.3 g) was added too. The whole was stirred at 3° C. for one hour and at room temperature for one hour, after which it was poured into 300 ml of water, extracted with ethyl ether which, after washing with NaCl saturated water and dehydration with sodium sulphate, was evaporated to dryness under reduced pressure. There was obtained 2 g (96%) of ethyl 2-methoxy-3-phenyl-3-(2-nitro-phenoxy)-propionate as an oil.

Workup

  1. extractionextracted with ethyl ether which
  2. washafter washing with NaCl saturated water and dehydration with sodium sulphate
  3. customwas evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1ec573d749114cda8576d405416f21a9
Source dataset
uspto-grants-1981_06
Patent number
US04271160

Reaction notes

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