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

HRID 1359252Notes

Reaction equation

HRID 1359252 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Sources & evidence

ORD record
ord-20f8f4076e9b41f599b8c063e40e46b5
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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