2-Methyl-7-(1-methylethylidene)-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-one → 7-Isopropyl-2-methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-one

HRID 1802701Notes

Reaction equation

HRID 1802701 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:13]3[C:12](=[O:14])[C:11](=[C:15]([CH3:17])[CH3:16])[CH2:10][C:9]=3[CH:8]=[CH:7][C:5]=2[N:6]=1>CO.C(OCC)(=O)C.[C].[Pd]>[CH:15]([CH:11]1[C:12](=[O:14])[C:13]2[C:4]3[O:3][C:2]([CH3:1])=[N:6][C:5]=3[CH:7]=[CH:8][C:9]=2[CH2:10]1)([CH3:17])[CH3:16]

Participants

4

Reactant 1

HCID 577812702-Methyl-7-(1-methylethylidene)-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-one

Product 1

HCID 577812527-Isopropyl-2-methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-oneYield 97%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 2-methyl-7-(1-methylethylidene)-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-one (677 mg, 2.98 mmol) in methanol/ethyl acetate (5/15 mL) was added a palladium-carbon powder (68 mg), and the mixture was stirred at room temperature for 40 hr under a hydrogen atmosphere. The catalyst was filtered off, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (662 mg, yield 97%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-cee3b20b19e2431190f1bbc05a5bdfd5
Source dataset
uspto-grants-2013_01
Patent number
US08349879B2

Reaction notes

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