2-Pyrrolidone → 1-(3,4,5-Trimethoxybenzyl)-2-oxopyrrolidine

HRID 323492Notes

Reaction equation

HRID 323492 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].C([Li])(CC)C.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([O:24][CH3:25])[C:21]=1[O:22][CH3:23])[CH2:17]Cl>O1CCCC1>[CH3:25][O:24][C:20]1[CH:19]=[C:16]([CH:15]=[C:14]([O:13][CH3:12])[C:21]=1[O:22][CH3:23])[CH2:17][N:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6]

Participants

5

Reactant 3

HCID 120252-PyrrolidoneHCID 774485-(Chloromethyl)-1,2,3-trimethoxybenzene2×HCID 178418400CID 53628100

Product 1

HCID 184646621-(3,4,5-Trimethoxybenzyl)-2-oxopyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Combine 2-pyrrolidinone (0.39 g, 4.62 mmol) and tetrahydrofuran (5 mL). Cool to −78° C. using a dry-ice/acetone bath. Add a solution of sec-butyl lithium (4.3 mL, 1.3 M in hexane, 5.55 mmol). After 15 minutes, add a solution of 3,4,5-trimethoxybenzyl chloride (1.00 g, 4.62 mmol) in tetrahydrofuran (5 mL). After the addition of 3,4,5-trimethoxybenzyl chloride is complete, heat to reflux. After 12 hours, cool the reaction mixture and partition between water and ethyl acetate. Separate the aqueous layer and extract 4 times with ethyl acetate. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to give the title compound.

Workup

  1. temperatureheat to reflux
  2. waitAfter 12 hours
  3. temperaturecool the reaction mixture
  4. custompartition between water and ethyl acetate
  5. customSeparate the aqueous layer
  6. extractionextract 4 times with ethyl acetate
  7. dry with materialDry the combined organic layers over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-af46923e759f476d96519dc417f768fa
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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