Lithium Hydroxide → 3-[7-(2-Ethoxy-3,5-diisopropylphenyl)-benzo[b]furan-2-yl]-but-2-enoic acid

HRID 1394584Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1394584
C([O:3][C:4](=[O:32])[CH:5]=[C:6]([C:8]1[O:12][C:11]2[C:13]([C:17]3[CH:22]=[C:21]([CH:23]([CH3:25])[CH3:24])[CH:20]=[C:19]([CH:26]([CH3:28])[CH3:27])[C:18]=3[O:29][CH2:30][CH3:31])=[CH:14][CH:15]=[CH:16][C:10]=2[CH:9]=1)[CH3:7])C.C1COCC1.[Li+].[OH-]>CO>[CH2:30]([O:29][C:18]1[C:19]([CH:26]([CH3:28])[CH3:27])=[CH:20][C:21]([CH:23]([CH3:24])[CH3:25])=[CH:22][C:17]=1[C:13]1[C:11]2[O:12][C:8]([C:6]([CH3:7])=[CH:5][C:4]([OH:32])=[O:3])=[CH:9][C:10]=2[CH:16]=[CH:15][CH:14]=1)[CH3:31]

Komponenten

5

Edukt 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 692208203-[7-(2-Ethoxy-3,5-diisopropylphenyl)-benzo[b]furan-2-yl]-but-2-enoic acid ethyl ester

Produkt 1

HCID 668965053-[7-(2-Ethoxy-3,5-diisopropylphenyl)-benzo[b]furan-2-yl]-but-2-enoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 0.450 mmol of 3-[7-(2-ethoxy-3,5-diisopropylphenyl)-benzo[b]furan-2-yl]-but-2-enoic acid ethyl ester, 3 mL of THF, 3 mL of methanol and 1 mL of LiOH (2N aqueous) was refluxed for 2 hours. After cooling at room temperature, the mixture was acidified to pH=2 and extracted with ethyl acetate. The organic layer was dried over MgSO4 and after evaporation of the solvents, the crude acid was recrystallized from acetonitrile. 3-[7-(2-Ethoxy-3,5-diisopropylphenyl)-benzo[b]furan-2-yl]-but-2-enoic acid was isolated as a white solid. 1H-NMR (CDCl3), δ: 7.65 (d, J=7.5 Hz, 1H, Ar—H), 7.56 (d, J=7.7 Hz, 1H, Ar—H), 7.33 (d, J=2.0 Hz, 1H, Ar—H), 7.29 (t, J=7.6 Hz, 1H, Ar—H), 7.16 (d, J=2.0 Hz, 1H, Ar—H), 7.11 (s, 1H, furan-H), 6.60 (s, 1H, C═C—H), 3.43 (m, 3H, CH3—CH—CH3, O—CH2—CH3), 2.95 (m, 1H, CH3—CH—CH3), 2.57 (s, 3H, C═C—CH3), 1.31 (d, J=6.9 Hz, 12H, CH3—CH—CH3), 0.97 (t, J=7.0 Hz, 3H, O—CH2—CH3).

Aufarbeitung

  1. temperaturewas refluxed for 2 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. customafter evaporation of the solvents
  5. customthe crude acid was recrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-6982a4de247f4d2abaaa5650e1096e99
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348359B2

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