1-(Trimethylsilyl)pyrrolidin-2-one → 1-(4'-Fluorophenoxycarbonyl)-2-pyrrolidinone

HRID 847221Notes

Reaction equation

HRID 847221 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=[O:3].C[Si](C)(C)[N:14]1[CH2:18][CH2:17][CH2:16][C:15]1=[O:19]>C1C=CC=CC=1>[F:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][C:2]([N:14]2[CH2:18][CH2:17][CH2:16][C:15]2=[O:19])=[O:3])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 844611-(Trimethylsilyl)pyrrolidin-2-oneHCID 27332564-Fluorophenyl chloroformate

Product 1

HCID 197515261-(4'-Fluorophenoxycarbonyl)-2-pyrrolidinoneYield 50.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 4-fluorophenyl chloroformate (3.55 g, 20.0 mmol) in anhydrous benzene (10 ml ) was added a solution of 1-trimethylsilyl-2-pyrrolidinone (3.46 g, 22.0 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. Recrystallization from 2-propanol afforded 2.24 g of colorless prisms. Yield 46.9%

Workup

  1. customThe reaction mixture was evaporated under reduced pressure to dryness
  2. customto give a solid material
  3. customRecrystallization from 2-propanol

Sources & evidence

ORD record
ord-abc39d5c65a6498b8a30a6ad2bb95382
Source dataset
uspto-grants-1992_08
Patent number
US05140041

Reaction notes

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