Triethylamine → HCID 54412960, compound

HRID 1762494Notes

Reaction equation

HRID 1762494 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][N:20]1[CH2:24][CH2:23][CH:22]([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:21]1=[O:44].C(N(CC)CC)C>C(O)C>[CH3:19][N:20]1[CH2:24][CH2:23][C:22](=[CH:8][C:7]2[CH:6]=[C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])[C:12]([OH:13])=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:10]=2)[C:21]1=[O:44]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 19608762HCID 19608762, compound

Product 1

HCID 54412960HCID 54412960, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.2 g of 3,5-di-tert-butyl-4-hydroxybenzaldehyde, 2.5 g of (N-methyl-2-pyrrolidone-3-yl)triphenylphosphonium bromide and 1.0 ml of triethylamine were heated under reflux in ethanol for two hours. After distilling the ethanol off, the residue was dissolved in chloroform, washed with water followed by a saturated saline solution and dried over anhydrous magnesium sulfate. After distilling the chloroform off, the residue was subjected to column chromatography with the use of silica gel and benzene/acetone and recrystallized from a mixture of ethyl acetate and hexane to give 1.0 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 materialdried over anhydrous magnesium sulfate
  5. distillationAfter distilling the chloroform off, the residue
  6. customrecrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-e0dadcb4dfb44cc1a2ad7ea32b68d360
Source dataset
uspto-grants-1989_05
Patent number
US04833160

Reaction notes

Loading…