5-(2-tert-Butoxycarbonylethenyl)furan-2-carboxylic acid benzyl ester → 5-(2-Tert-butoxycarbonylethyl)-furan-2-carboxylic acid

HRID 332604Notes

Reaction equation

HRID 332604 reaction equation
C([O:8][C:9]([C:11]1[O:12][C:13]([CH:16]=[CH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:14][CH:15]=1)=[O:10])C1C=CC=CC=1>CO.[Pd]>[C:21]([O:20][C:18]([CH2:17][CH2:16][C:13]1[O:12][C:11]([C:9]([OH:10])=[O:8])=[CH:15][CH:14]=1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 1

HCID 779345505-(2-tert-Butoxycarbonylethenyl)furan-2-carboxylic acid benzyl ester

Product 1

HCID 683202805-(2-Tert-butoxycarbonylethyl)-furan-2-carboxylic acidYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

5-(2-tert-Butoxycarbonylethenyl)furan-2-carboxylic acid benzyl ester (0.97 g, 2.80 mmol) was dissolved in methanol (50 mL), 10% palladium/carbon (0.1 g) was added, and the mixture was stirred at room temperature for 2 hours under a hydrogen atmosphere. After completion of the reaction, palladium/carbon was removed by celite filtration, and the solvent was evaporated under reduced pressure to give the title compound (0.66 g).

Workup

  1. customwas removed by celite filtration
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5332808bdf014035bcfa2b47391904ec
Source dataset
uspto-grants-2014_11
Patent number
US08877805B2

Reaction notes

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