HCID 59527540, compound → HCID 59527136, compound

HRID 384448Notes

Reaction equation

HRID 384448 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9](/[CH:11]=[CH:12]/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1>C(O)C.[Pd]>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 59527540HCID 59527540, compound

Product 1

HCID 59527136HCID 59527136, compoundYield 57.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl (2E,4E)-5-(2,3-dihydro-1,4-benzodioxin-6-yl)penta-2,4-dienoate (5.00 g) in ethanol (100 mL) was added 10% palladium-activated carbon (1.0 g), followed by stirring at room temperature under hydrogen atmosphere (4 atm.) for 5 hours. The catalyst was removed by filtration, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=85/15) to obtain ethyl 5-(2,3-dihydro-1,4-benzodioxin-6-yl)pentanoate (2.94 g).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=85/15)

Sources & evidence

ORD record
ord-6b92ec0de1c2486db49362b5fa5a16a4
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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