HCID 86668160, compound → HCID 68108957, compound

HRID 385054Notes

Reaction equation

HRID 385054 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([C:15]#[CH:16])[C:12]=1[O:13][CH3:14])[C:6]([O:8][CH3:9])=[O:7])#[N:2]>O1CCCC1.[C].[Pd]>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH2:15][CH3:16])[C:12]=1[O:13][CH3:14])[C:6]([O:8][CH3:9])=[O:7])#[N:2]

Participants

4

Reactant 1

HCID 86668160HCID 86668160, compound

Product 1

HCID 68108957HCID 68108957, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-cyano-5-ethynyl-4-methoxybenzoate (475 mg) was dissolved in tetrahydrofuran (10 mL), and 5% palladium-carbon (150 mg) was added to the solution, and then the mixture was stirred under a hydrogen atmosphere at room temperature for 30 minutes. The reaction solution was filtered, and then the solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to obtain the title compound (480 mg) as a colorless crystal.

Workup

  1. filtrationThe reaction solution was filtered
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-9ef1828c13314649b118b18ca126e325
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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