Tetrahydrofuran → HCID 66884709, compound

HRID 241365Notes

Reaction equation

HRID 241365 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:10][C:5]=2[S:4][C:3]=1[CH:15]=[CH:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[CH:26][C:27]([O:29][CH3:30])=[O:28])=[C:21]([CH3:31])[CH:20]=1)=[O:18].C1COCC1>CO.[C].[Pd]>[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([F:13])([F:14])[F:12])=[CH:10][C:5]=2[S:4][C:3]=1[CH2:15][CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[C:21]([CH3:31])[CH:20]=1)=[O:18]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 66883212HCID 66883212, compound

Product 1

HCID 66884709HCID 66884709, compoundYield 44.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Methyl 3-[4-[3-[3-methyl-6-(trifluoromethyl)benzothiophen-2-yl]propenoyl]-2-methylphenyl]acrylate (85 mg, 0.19 mmol) was hydrogenated in MeOH (1 mL)/THF (1 mL) for 1 hour at room temperature using 10% palladium-carbon (17 mg) as a catalyst. After removal of the catalyst by filtration, the filtrate was concentrated to dryness. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1), to give the titled compound as a pale yellow crystal (38 mg, yield 44%).

Workup

  1. customfor 1 hour
  2. customat room temperature
  3. customAfter removal of the catalyst
  4. filtrationby filtration
  5. concentrationthe filtrate was concentrated to dryness
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-fef4467113ab4446adb0c6432888d900
Source dataset
uspto-grants-2014_02
Patent number
US08648208B2

Reaction notes

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