Potassium Carbonate → Methyl 3-[3,5-Diisopropyl-4-(1-phenyltetrazol-5-yloxy)benzoyl]propionate

HRID 976351Notes

Reaction equation

HRID 976351 reaction equation
[OH:1][C:2]1[C:15]([CH:16]([CH3:18])[CH3:17])=[CH:14][C:5]([C:6]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:7])=[CH:4][C:3]=1[CH:19]([CH3:21])[CH3:20].Cl[C:23]1[N:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:26]=[N:25][N:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:16]([C:15]1[CH:14]=[C:5]([CH:4]=[C:3]([CH:19]([CH3:21])[CH3:20])[C:2]=1[O:1][C:23]1[N:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:26]=[N:25][N:24]=1)[C:6]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 842621H-Tetrazole, 5-chloro-1-phenyl-HCID 19967177Methyl 4-(4-hydroxy-3,5-diisopropylphenyl)-4-oxobutanoate

Product 1

HCID 19967146Methyl 3-[3,5-Diisopropyl-4-(1-phenyltetrazol-5-yloxy)benzoyl]propionateYield 85.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

11 g of Methyl 3-(4-hydroxy-3,5-diisopropylbenzoyl]propionate was dissolved in 200 ml of N,N-dimethylformamide, followed by the addition of 8.15 g of 5-chloro-1-phenyl-1H-tetrazol and 10.4 g of potassium carbonate. The obtained mixture was stirred for 1 hour under heating, cooled to room temperature by allowing to stand and poured onto ice-water. The resultant mixture was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent. The obtained residue was purified by silica gel chromatography (developer: 20% ethyl acetate/n-hexane) to give 14.1 g of the title compound as a white solid.

Workup

  1. temperatureunder heating
  2. additionpoured onto ice-water
  3. extractionThe resultant mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with a saturated aqueous solution of common salt
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe obtained residue was purified by silica gel chromatography (developer: 20% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-4bcc7cdbe3e64846bedb6f0ba6865d75
Source dataset
uspto-grants-1997_03
Patent number
US05612356

Reaction notes

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