Triethylamine → N-Methoxy-3-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2-pyrrolidone

HRID 1762495Notes

Reaction equation

HRID 1762495 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[Br-].[CH3:19][O:20][N:21]1[CH2:25][CH2:24][CH:23]([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:22]1=[O:45].C(N(CC)CC)C>C(O)C>[CH3:19][O:20][N:21]1[CH2:25][CH2:24][C:23](=[CH:8][C:7]2[CH:6]=[C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[C:12]([OH:13])=[C:11]([C:14]([CH3:15])([CH3:16])[CH3:17])[CH:10]=2)[C:22]1=[O:45]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 20041535(1-Methoxy-2-oxopyrrolidin-3-yl)(triphenyl)phosphanium bromide

Product 1

HCID 119572N-Methoxy-3-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2-pyrrolidoneYield 67.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

27.6 g of 3,5-di-tert-butyl-4-hydroxybenzaldehyde, 54.0 g of (N-methoxy-2-pyrrolidone-3-yl)triphenylphosphonium bromide and 33.0 ml of triethylamine were heated at 50° C. in ethanol for four hours. After distilling the ethanol off, the residue was dissolved in chloroform, washed with water and then a saturated saline solution and dried over anhydrous magnesium sulfate. After distilling the chloroform off, the residue was treated with the column chromatography, using silica gel and a carrier liquid of benzene and acetone and recrystallized with a mixture of ethyl acetate and hexane to give 26.5 g of the title compound.

Workup

  1. distillationAfter distilling the ethanol off, the residue
  2. dissolutionwas dissolved in chloroform
  3. washwashed with water
  4. dry with materiala saturated saline solution and dried over anhydrous magnesium sulfate
  5. distillationAfter distilling the chloroform off, the residue
  6. additionwas treated with the column chromatography
  7. customa carrier liquid of benzene and acetone and recrystallized with a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-31c9ad1a2108474d956739885bae8e1f
Source dataset
uspto-grants-1989_05
Patent number
US04833160

Reaction notes

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