Water → HCID 53689480, compound

HRID 1648417Notes

Reaction equation

HRID 1648417 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:18]=[CH:17][CH:16]=[CH:15][C:7]=1[CH2:8]P(=O)(OC)OC)([O-:5])=[O:4].[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O.O>O1CCCC1>[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=[CH:8][C:7]1[CH:15]=[CH:16][CH:17]=[CH:18][C:6]=1[N+:3]([O-:5])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 69962-ChlorobenzaldehydeHCID 24758Sodium hydrideHCID 13227377Dimethyl [(2-nitrophenyl)methyl]phosphonate

Product 1

HCID 53689480HCID 53689480, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.63 g of 60 wt % sodium hydride were added to 20 ml of tetrahydrofuran under stirring at room temperature, followed by cooling thereof to 0° C. and drop-wise addition thereto of a solution of 8 g of dimethyl 2-nitrobenzylphosphonate in 20 ml of tetrahydrofuran. After completion of the drop-wise addition, the reaction mixture was stirred at 0° C. for 30 minutes, followed by drop-wise addition thereto of 6.2 g of 2-chlorobenzaldehyde. After completion of the drop-wise addition, the resulting mixture was gradually heated up to room temperature, at which stirring was then continued for 17 hours. The reaction mixture was poured into water, subjected to extraction with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was purified twice by silica gel column chromatography (first developing solvent:methylene chloride:hexane=7:3, and second developing solvent:methylene chloride:hexane=3:1) to obtain 5.8 g of 2-chloro-2'-nitrostilbene.

Workup

  1. temperatureby cooling
  2. customto 0° C.
  3. additionaddition
  4. additionAfter completion of the drop-wise addition
  5. stirringthe reaction mixture was stirred at 0° C. for 30 minutes
  6. additionfollowed by drop-wise addition
  7. additionAfter completion of the drop-wise addition
  8. temperaturethe resulting mixture was gradually heated up to room temperature, at which
  9. stirringstirring
  10. extractionsubjected to extraction with ethyl acetate
  11. washwashed with water
  12. dry with materialdried over anhydrous sodium sulfate
  13. distillationThe solvent was distilled off under reduced pressure
  14. customThe resulting residue was purified twice by silica gel column chromatography (first developing solvent:methylene chloride:hexane=7:3, and second developing solvent:methylene chloride:hexane=3:1)

Sources & evidence

ORD record
ord-33d627430c984cc5bfe4315e146d0394
Source dataset
uspto-grants-1995_07
Patent number
US05436267

Reaction notes

Loading…