Guaiacol → 1-Pyrrolidinecarboxylic acid, 2-oxo-, 2-methoxyphenyl ester

HRID 847219Notes

Reaction equation

HRID 847219 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13].N1C=CC=CC=1.C[Si](C)(C)[N:22]1[CH2:26][CH2:25][CH2:24][C:23]1=[O:27]>C1C=CC=CC=1>[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:23]([N:22]1[CH2:26][CH2:25][CH2:24][C:1]1=[O:2])=[O:27]

Participants

6

Reactant 4

HCID 460GuaiacolHCID 1049PyridineHCID 6371PhosgeneHCID 844611-(Trimethylsilyl)pyrrolidin-2-one

Product 1

HCID 98160981-Pyrrolidinecarboxylic acid, 2-oxo-, 2-methoxyphenyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent4×

Procedure

To a solution of phosgen (6.27 g, 63.3 mmol) in anhydrous benzene (30 ml) was dropwise added under ice-cooling a solution of 2-methoxyphenol (7.86 g, 63.3 mmol) and purified pyridine (5.00 g, 63.3 mmol) in anhydrous benzene (20 ml). The mixture was stirred overnight at room temperature. From a reaction solution were separated white precipitates by filtration, and a filtrate was evaporated under reduced pressure to give a colorless oily material. The oily material was dissolved in anhydrous benzene (20 ml), to which was added a solution of 1-trimethylsilyl-2-pyrrolidinone (9.66 g, 63.3 mmol) in anhydrous benzene (10 ml). The mixture was stirred at room temperature for 30 min. The reaction mixture was evaporated under reduced pressure to dryness to give a solid material. The desired product was separated using column chromatography on silica gel (eluted with benzene-acetone 20:1→1:1).

Workup

  1. customFrom a reaction solution were separated white
  2. customprecipitates by filtration
  3. customa filtrate was evaporated under reduced pressure
  4. customto give a colorless oily material
  5. stirringThe mixture was stirred at room temperature for 30 min
  6. customThe reaction mixture was evaporated under reduced pressure to dryness
  7. customto give a solid material
  8. customThe desired product was separated

Sources & evidence

ORD record
ord-34a046a3a8834c87ae5213a3f7b562c3
Source dataset
uspto-grants-1992_08
Patent number
US05140041

Reaction notes

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