HCID 53825491, compound → HCID 19369855, compound

HRID 849034Notes

Reaction equation

HRID 849034 reaction equation
[C:1]([O:4][C:5]1[C:6]([O:27][CH3:28])=[C:7]([O:25][CH3:26])[C:8]2[O:12][C:11]([CH:14]=[CH:15][CH:16]=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH3:13])[CH2:10][C:9]=2[C:23]=1[CH3:24])(=[O:3])[CH3:2]>C(O)C.[C].[Pd]>[C:1]([O:4][C:5]1[C:6]([O:27][CH3:28])=[C:7]([O:25][CH3:26])[C:8]2[O:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH3:13])[CH2:10][C:9]=2[C:23]=1[CH3:24])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 53825491HCID 53825491, compound

Product 1

HCID 19369855HCID 19369855, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

5% palladium-carbon (0.1 g) was added to a solution of ethyl 5-(5-acetoxy-2,3-dihydro-6,7-dimethoxy-2,4-dimethylbenzofuran-2-yl)pentadienoate (1.3 g) in ethanol (30 ml), and the mixture was stirred under an atmosphere of hydrogen at 50° C. for 5 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate 7:3) to obtain the title compound (1.1 g, 86%) as an oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate 7:3)

Sources & evidence

ORD record
ord-ef71441c63094429a650af6d10a5a80f
Source dataset
uspto-grants-2000_01
Patent number
US06011046

Reaction notes

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