Triethylamine → HCID 53762281, compound

HRID 1109298Notes

Reaction equation

HRID 1109298 reaction equation
[Br-].[C:2]([N:5]1[CH2:9][CH2:8][CH:7]([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:6]1=[O:29])(=[O:4])[CH3:3].[CH:30]([C:33]1[CH:34]=[C:35]([CH:38]=[C:39]([CH:42]([CH3:44])[CH3:43])[C:40]=1[OH:41])[CH:36]=O)([CH3:32])[CH3:31].C(N(CC)CC)C.C(OCC)(=O)C>C(O)C.O>[C:2]([N:5]1[CH2:9][CH2:8][C:7](=[CH:36][C:35]2[CH:34]=[C:33]([CH:30]([CH3:32])[CH3:31])[C:40]([OH:41])=[C:39]([CH:42]([CH3:44])[CH3:43])[CH:38]=2)[C:6]1=[O:29])(=[O:4])[CH3:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 827124-Hydroxy-3,5-bis(isopropyl)benzaldehydeHCID 19022168HCID 19022168, compound

Product 1

HCID 53762281HCID 53762281, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5.90 g (6 mmol) of (1-acetyl-2-oxopyrrolidin-3-yl)triphenylphosphonium bromide in ethanol (12 ml) were added 1.24 g (6 mmol) of 3,5-di-isopropyl-4-hydroxybenzaldehyde and 1.67 ml (12 mmol) of triethylamine, and the mixture was stirred with heating at 60° C. for 2 hours. The reaction mixture was evaporated to give a residue, which was added with ethyl acetate and water. The ethyl acetate layer was washed with water, dried over magnesium sulfate and evaporated to give a residue, which was chromatographed on silica gel (toluene/ethyl acetate=4/1) to give 857 mg of the objective compound in 45% yield.

Workup

  1. customThe reaction mixture was evaporated
  2. customto give a residue, which
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto give a residue, which
  7. customwas chromatographed on silica gel (toluene/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-5c53b58c0ecc480c89e07eb531e0325e
Source dataset
uspto-grants-1994_06
Patent number
US05319100

Reaction notes

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