Triethylamine → 4-(cyclopent-1-en-1-yl)benzoic acid

HRID 1174971Notes

Reaction equation

HRID 1174971 reaction equation
I[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH:11]1[CH2:15][CH2:14][CH2:13][CH:12]=1.CCN(CC)CC.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C1(C)C=CC=CC=1.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:11]1([C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)[CH2:15][CH2:14][CH2:13][CH:12]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8882CyclopenteneHCID 120854-Iodobenzoic acidHCID 80271Tri-o-tolylphosphine

Product 1

HCID 2779144-(cyclopent-1-en-1-yl)benzoic acidYield 69.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

In a sealed tube is added 4-iodobenzoic acid (5.0 g, 20.16 mmol), cyclopentene (17.8 mL, 2101.6 mmol), Et3N (8.4 mL, 60.48 mmol) in toluene (100 mL). It is purged with N2 for 15 min. Pd(OAc)2 (0.23 g, 1.01 mmol) and P(o-Tol)3 (0.61 g, 2.01 mmol) are added. The reaction is stirred at 120° C. overnight. It is diluted with EtOAc, washed with 1M HCl, H2O, and brine. Purification of the crude material by chromatography gives the title compound (2.63 g, 69%).

Workup

  1. customIt is purged with N2 for 15 min
  2. washwashed with 1M HCl, H2O, and brine
  3. customPurification of the crude material by chromatography

Sources & evidence

ORD record
ord-953b68159630436fb3c650c97c7f6b4a
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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