3-(2-Ethylbutyl)-1-cyclobutenecarboxylic acid → 3-(2-Ethylbutyl)cyclobutanecarboxylic acid

HRID 1912090Notes

Reaction equation

HRID 1912090 reaction equation
[CH2:1]([CH:3]([CH2:12][CH3:13])[CH2:4][CH:5]1[CH2:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6]1)[CH3:2]>O1CCCC1.[Pd]>[CH2:12]([CH:3]([CH2:1][CH3:2])[CH2:4][CH:5]1[CH2:6][CH:7]([C:9]([OH:11])=[O:10])[CH2:8]1)[CH3:13]

Participants

4

Reactant 1

HCID 866750483-(2-Ethylbutyl)-1-cyclobutenecarboxylic acid

Product 1

HCID 866750493-(2-Ethylbutyl)cyclobutanecarboxylic acidYield 63.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

3-(2-Ethylbutyl)-1-cyclobutenecarboxylic acid (39.0 g) was dissolved in tetrahydrofuran (200 mL). To the solution was added 5 w/w % palladium on activated carbon (5.5 g). The mixture was stirred at RT overnight under hydrogen atmosphere (1 atm). The 5 w/w % palladium on activated carbon was filtered off using Celite and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/4→1/2) to give the title compound (25.2 g).

Workup

  1. filtrationwas filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/4→1/2)

Sources & evidence

ORD record
ord-a446b6416748441e90744d678b198ff1
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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