Triethylamine → HCID 54460719, compound

HRID 1109353Notes

Reaction equation

HRID 1109353 reaction equation
[C:1]([N:4]1[CH2:8][CH2:7][CH:6](Br)[C:5]1=[O:10])(=[O:3])[NH2:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:30]([C:34]1[CH:35]=[C:36]([CH:39]=[C:40]([C:43]([CH3:46])([CH3:45])[CH3:44])[C:41]=1[OH:42])[CH:37]=O)([CH3:33])([CH3:32])[CH3:31].C(N(CC)CC)C>C1COCC1.C(O)C>[C:1]([N:4]1[CH2:8][CH2:7][C:6](=[CH:37][C:36]2[CH:35]=[C:34]([C:30]([CH3:31])([CH3:33])[CH3:32])[C:41]([OH:42])=[C:40]([C:43]([CH3:46])([CH3:45])[CH3:44])[CH:39]=2)[C:5]1=[O:10])(=[O:3])[NH2:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 15230361HCID 15230361, compound

Product 1

HCID 54460719HCID 54460719, compoundYield 60.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 2.0 g of N-carbamoyl-3-bromopyrrolidin-2-one (9.7 mmole) and 2.78 g of triphenylphosphine (10.6 mmole) in 30 ml of THF was stirred under heating at 70° C. for 20 hours. The reaction mixture was cooled down to room temperature, then the precipitated crystals were collected. The obtained Wittig salt (1.34 g, 2.86 mmole), 3,5-di-tert-butyl-4-hydroxybenzaldehyde (670 mg, 2.86 mmole), and triethylamine (580 mg, 5.73 mmole) were dissolved into 60 ml of ethanol, and the mixture was stirred under heating at 70° C. for 2 hours. The reaction mixture was evaporated, then the residue was dissolved into ethyl acetate, which was washed with water and saturated brine, dried over magnesium sulfate, and evaporated. The residue was separated by using silica gel chromatography (toluene:ethyl acetate=3:1) and recrystallized from dichloromethane-n-hexane, whereby 600 mg of the objective compound was obtained in 17.1% yield. The physical constants are described on Table 1.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. customthe precipitated crystals were collected
  3. temperatureunder heating at 70° C. for 2 hours
  4. customThe reaction mixture was evaporated
  5. dissolutionthe residue was dissolved into ethyl acetate, which
  6. washwas washed with water and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customThe residue was separated
  10. customrecrystallized from dichloromethane-n-hexane

Sources & evidence

ORD record
ord-46aa0f2d8bb743b08f828b9f178f2bd1
Source dataset
uspto-grants-1994_06
Patent number
US05319099

Reaction notes

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