Tetrahydrofuran → HCID 20209683, compound

HRID 1800754Notes

Reaction equation

HRID 1800754 reaction equation
[C:1]([CH:3]=[CH:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2].O1CCCC1>C(O)C.[C].[Pd]>[C:1]([CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 68417867HCID 68417867, compound

Product 1

HCID 20209683HCID 20209683, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of the above-mentioned crude product of methyl 3-(2-cyanoethenyl)benzoate in ethanol (45 mL)/tetrahydrofuran (15 mL) was added 10% palladium-carbon (648 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere (1 atm) for 2 hr. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→75/25), and the fractions containing the object product were concentrated under reduced pressure to give the title compound (2.03 g, 88%) as a colorless oil.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→75/25)
  4. additionthe fractions containing the object product
  5. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-3e59e15d20974eabb618acb04c97bac3
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

Loading…