1-Methyl-1,4-cyclohexadiene → HCID 59293873, compound

HRID 1664651Notes

Reaction equation

HRID 1664651 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH:14]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH2:13][C:12]2=[O:23])C1C=CC=CC=1.CC1CC=CCC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH:14]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH2:13][C:12]2=[O:23]

Participants

5

Reactant 2

HCID 780061-Methyl-1,4-cyclohexadieneHCID 59293864HCID 59293864, compound

Product 1

HCID 59293873HCID 59293873, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of methyl [5-(benzyloxy)-3-oxo-2,3-dihydro-1H-inden-1-yl]acetate (1.0 g, 3.22 mmol) and 1-methylcyclohexa-1,4-diene (10 ml, 89 mmol) in ethanol (30 ml) was added 10% Pd/C (0.686 g, 0.644 mmol), and the mix was stirred at 55° C. After 1 hour the mix was filtered through a bed of Celite, washing with ethanol The filtrate was concentrated and the residue was concentrated from ether-hexane to give methyl (5-hydroxy-3-oxo-2,3-dihydro-1H-inden-1-yl)acetate. LC-MS for C12H12O4: calc 220, found 221 [M+H].

Workup

  1. filtrationAfter 1 hour the mix was filtered through a bed of Celite
  2. washwashing with ethanol The filtrate
  3. concentrationwas concentrated
  4. concentrationthe residue was concentrated from ether-hexane

Sources & evidence

ORD record
ord-af21c9de00a541f097d091cb5aaf687a
Source dataset
uspto-grants-2011_10
Patent number
US08039484B2

Reaction notes

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