Diethyl Ether → 1-(4-Chlorophenyl)-3-mesyloxymethyl-2-pyrrolidinone

HRID 1740379Notes

Reaction equation

HRID 1740379 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[C:14]2=[O:20])=[CH:9][CH:8]=1.C(N(CC)CC)C.C(OCC)C>ClCCl>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:17][CH2:16][CH:15]([CH2:18][O:19][S:2]([CH3:1])(=[O:4])=[O:3])[C:14]2=[O:20])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 218386441-(4-Chlorophenyl)-3-(hydroxymethyl)pyrrolidin-2-one

Product 1

HCID 218386401-(4-Chlorophenyl)-3-mesyloxymethyl-2-pyrrolidinoneYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under ice-cooling, 14.0 g of methanesulfonyl chloride was added dropwise to a solution of 23.2 g of 1-(4-chlorophenyl)-3-hydroxymethyl-2-pyrrolidinone and 12.5 g of triethylamine in 200 mL of dichloromethane. After 2 hours, the reaction mixture was washed with water, dried over anhydrous magnesium sulfate and concentrated to give crystals. The crystals were sludged with diethyl ether and collected by filtration. The crystals were washed with diethyl ether and dried in vacuo to give 29.8 g of the title compound.

Workup

  1. temperatureUnder ice-cooling
  2. washthe reaction mixture was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give crystals
  6. filtrationcollected by filtration
  7. washThe crystals were washed with diethyl ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-9f888bf2e4a44ae0a1827dc41150fb45
Source dataset
uspto-grants-1999_10
Patent number
US05969138

Reaction notes

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