2-Pyrrolidone → 3-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2-pyrrolidone

HRID 1708253Notes

Reaction equation

HRID 1708253 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].C(=O)([O-])OC.[Mg+2].COC(=O)[O-].[C:18]([C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:29]=1[OH:30])[CH:25]=O)([CH3:21])([CH3:20])[CH3:19]>CN(C=O)C>[CH3:21][C:18]([C:22]1[CH:23]=[C:24]([CH:25]=[C:3]2[CH2:4][CH2:5][NH:1][C:2]2=[O:6])[CH:27]=[C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:29]=1[OH:30])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 120252-PyrrolidoneHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 167017Carbonic acid, monomethyl ester, magnesium salt (2:1)

Product 1

HCID 538962973-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2-pyrrolidoneYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, 1.52 ml of 2-pyrrolidinone was added to a solution of 32 ml of 2M magnesium methyl carbonate in DMF and 5.86 g of 3,5-di-tert-butyl-4-hydroxybenzaldehyde. The resultant mixture was stirred at reflux temperature for six days and then allowed to cool. The cooled reaction mixture was poured into 40 g of ice containing 10 ml concentrated hydrochloric acid and then extracted with chloroform. The chloroform layer was collected, filtered and the filtrate was concentrated. The resulting residue was purified by silica gel chromatography and recrystallized from ethyl acetate to give the desired titled product (21% yield), m.p. 216°-218° C.

Workup

  1. temperatureat reflux temperature for six days
  2. temperatureto cool
  3. customThe cooled reaction mixture
  4. extractionextracted with chloroform
  5. customThe chloroform layer was collected
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe resulting residue was purified by silica gel chromatography
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1849bbbe47cc4aff89f2453e5c8e1a81
Source dataset
uspto-grants-1994_10
Patent number
US05356917

Reaction notes

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