Potassium Hydroxide → [6-(3-Pentyl-benzofuran-2-yl)-naphthalen-2-yloxy]-acetic acid

HRID 1359252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1359252
C([O:3][C:4](=[O:31])[CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]3[O:18][C:19]4[CH:30]=[CH:29][CH:28]=[CH:27][C:20]=4[C:21]=3[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:13]=2)[CH:8]=1)C.[OH-].[K+]>C1COCC1.O>[CH2:22]([C:21]1[C:20]2[CH:27]=[CH:28][CH:29]=[CH:30][C:19]=2[O:18][C:17]=1[C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:6][CH2:5][C:4]([OH:31])=[O:3])[CH:16]=[CH:15]2)[CH2:23][CH2:24][CH2:25][CH3:26]

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 69830661[6-(3-Pentyl-benzofuran-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester

Produkt 1

HCID 10157100[6-(3-Pentyl-benzofuran-2-yl)-naphthalen-2-yloxy]-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Following the procedure described in Step 4 of Example 6, [6-(3-Pentyl-benzofuran-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester (0.34 g, 0.82 mmol), was hydrolyzed with potassium hydroxide (0.50 g, 8.9 mmol) in THF (20 mL) and water (10 mL). The title compound was obtained as an off-white solid (0.28 g), mp 163-165° C. Mass spectrum (+APCl, [M+H]+) m/z 389. 1HNMR (400 MHz, DMSO-d6): δ13.15 (br s, 1H), 8.24 (s, 1H), 7.99 (d, 1H, J=9.0 Hz), 7.93 (d, 1H, J=8.8 Hz), 7.85 (dd, 1H, J=8.5, 1.7 Hz), 7.69-7.66 (m, 1H), 7.59 (d, 1H, J=7.8 Hz), 7.35-7.25 (m, 4H), 4.82 (s, 2H), 2.98 (t, 2H, J=7.6 Hz), 1.72 (p, 2H, J=7.3 Hz), 1.42-1.27 (m, 4H), and 0.83 ppm (t, 3H, J=7.1 Hz). Elemental Analysis for C25H24O4.0.4H2O: Calculated: C, 75.89; H, 6.32; N, 0.00. Found: C, 75.9; H, 6.07; N, 0.17.

Quellen und Nachweise

ORD-Eintrag
ord-20f8f4076e9b41f599b8c063e40e46b5
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06599925B2

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