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

HRID 1174971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1174971
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

Komponenten

8

Edukt 4

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

Produkt 1

HCID 2779144-(cyclopent-1-en-1-yl)benzoic acidAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-953b68159630436fb3c650c97c7f6b4a
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07838543B2

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