Water → HCID 53873602, compound

HRID 1679993Notes

Reaction equation

HRID 1679993 reaction equation
[Na].[OH:2][C:3]([CH:8]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17])=[CH:4][N+:5]([O-:7])=[O:6].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].O>C1COCC1>[CH2:29]([O:28][C:26]([CH2:25][O:2][C:3]([CH:8]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17])=[CH:4][N+:5]([O-:7])=[O:6])=[O:27])[CH3:30]

Participants

5

Reactant 3

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 70579319HCID 70579319, compound

Product 1

HCID 53873602HCID 53873602, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To 3.23 g of 2-hydroxy-3-phenyl-3-(2-methoxy-phenoxy)-1-nitropropene sodium salt dissolved in 50 ml of anhydrous THF there was added at 0° C. 16.7 g of ethyl bromoacetate. After 2 hours at 0° C. the mixture was stirred at room temperature for 48 hours. The mixture was poured into water and extracted with ethyl acetate. The organic extracts were washed with water, dried over Na2SO4 and concentrated to dryness. The residue was separated by column chromatography on silica gel (mobile phase:ethyl acetate/cyclohexane 1/1), to obtain 2.70 g of 2-ethoxycarbonylmethyloxy-3-phenyl-3-(2-methoxy-phenoxy)-1-nitropropene (oil). Yield 70%.

Workup

  1. additionwas added at 0° C
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe residue was separated by column chromatography on silica gel (mobile phase:ethyl acetate/cyclohexane 1/1)

Sources & evidence

ORD record
ord-1b58525e8d1d4e58819ba76c2cada503
Source dataset
uspto-grants-1981_06
Patent number
US04271160

Reaction notes

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