Potassium Carbonate → HCID 54443158, compound

HRID 1779327Notes

Reaction equation

HRID 1779327 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]=[C:13]([P:20]([O:24][CH3:25])([O:22][CH3:23])=[O:21])[C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])[CH:6]=[C:7]([O:10][CH3:11])[C:8]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].[CH3:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38]Cl)=[CH:36][CH:35]=1>C(#N)C>[CH3:11][O:10][C:7]1[CH:6]=[C:5]([CH:12]=[C:13]([P:20]([O:22][CH3:23])([O:24][CH3:25])=[O:21])[C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH2:38][C:37]1[CH:40]=[CH:41][C:34]([O:33][CH3:32])=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chloride2×HCID 54081214HCID 54081214, compound

Product 1

HCID 54443158HCID 54443158, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Isopropyl 3-(3,5-dimethoxy-4-hydroxyphenyl)-2-(dimethoxy-phosphinyl)propenoate (4 g; 0.01 mol; Table 1, No. 10) was dissolved in 60 ml of acetonitrile, and potassium carbonate (4.45 g; 0.032 mol) and 4-methoxybenzyl chloride (1.4 ml; 0.011 mol) were added and the mixture was initially stirred at room temperature for 8 hours. To complete the reaction, 0.7 ml of 4-methoxybenzyl chloride was added, followed by stirring for 4 hours, after which the result of a thin-layer chromatography showed that the reaction was complete. The filtrate after removal of potassium carbonate by filtration was evaporated to dryness under reduced pressure, and the residue is chromatographed (SiO2 ; CH2CI2 : AcOEt=8:2). This resulted in a slowly crystallizing oil which, on solidification, had a melting point of 68° to 69° C.

Workup

  1. additionwas added
  2. stirringby stirring for 4 hours
  3. customafter which the result of a thin-layer chromatography
  4. customThe filtrate after removal of potassium carbonate
  5. filtrationby filtration
  6. customwas evaporated to dryness under reduced pressure
  7. customthe residue is chromatographed (SiO2 ; CH2CI2 : AcOEt=8:2)
  8. customThis resulted in
  9. customa slowly crystallizing oil which

Sources & evidence

ORD record
ord-6f33b52dfcb84989a3399107ee29d0aa
Source dataset
uspto-grants-1997_05
Patent number
US05627173

Reaction notes

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