2-Pyrrolidone → 2-Pyrrolidinone, 1-((4-methoxyphenyl)methyl)-

HRID 714798Notes

Reaction equation

HRID 714798 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].O1CCCC1.CN(C)C=O.[H-].[Na+].[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1>O>[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:1]2[CH2:5][CH2:4][CH2:3][C:2]2=[O:6])=[CH:23][CH:22]=1

Participants

6

Procedure

To a solution of pyrrolidin-2-one (15 g) in a mixed solvent of tetrahydrofuran/N,N-dimethylformamide (1/1, 100 mL) was added sodium hydride (60% in mineral oil, 8.5 g) at 0° C. under nitrogen atmosphere, and the mixture was stirred for 30 min. p-Methoxybenzyl chloride (33 g) was added thereto at the same temperature, and the mixture was stirred at room temperature for 5 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (28 g).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d2221889fc454001aa3e4f893520ab3d
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

Loading…