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

HRID 976352Notes

Reaction equation

HRID 976352 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:15]=[C:16]([CH:30]([CH3:32])[CH3:31])[C:17]=1OC1N(C2C=CC=CC=2)N=NN=1)[C:7]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[O:8])([CH3:3])[CH3:2]>C1C=CC=CC=1.[Pd]>[CH:1]([C:4]1[CH:5]=[C:6]([CH:15]=[C:16]([CH:30]([CH3:32])[CH3:31])[CH:17]=1)[C:7]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[O:8])([CH3:3])[CH3:2]

Participants

4

Reactant 1

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

Product 1

HCID 19967165Methyl 3-(3,5-diisopropylbenzoyl)propionateYield 71.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 241BenzeneSolvent

Procedure

14.1 g of Methyl 3-[3,5-diisopropyl-4-(1-phenyltetrazol-5-yloxy)benzoyl]propionate was dissolved in 100 ml of benzene, followed by the addition of 10 g of 10% palladium/carbon. The obtained mixture was subjected to hydrogenation under a pressure of 3 kg/cm2, at room temperature for 14 hours. The reaction mixture thus obtained was filtered to remove the catalyst. The filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (developer: 3% ethyl acetate/n-hexane) to give 6.4 g of the title compound as a colorless oil.

Workup

  1. customThe reaction mixture thus obtained
  2. filtrationwas filtered
  3. customto remove the catalyst
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel chromatography (developer: 3% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-3a3b8643fb8147ee844d1f66562560c3
Source dataset
uspto-grants-1997_03
Patent number
US05612356

Reaction notes

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