Potassium Hydroxide → 2-{[1-Chloro-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetic acid

HRID 1359233Notes

Reaction equation

HRID 1359233 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=4[C:16]=3[C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:27][CH2:28][C:29]([O:31]CC)=[O:30].[OH-].[K+]>C1COCC1.O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=4[C:16]=3[C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:27][CH2:28][C:29]([OH:31])=[O:30]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 18182776Ethyl 2-{[1-chloro-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetate

Product 1

HCID 101602322-{[1-Chloro-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure described in Step 4 of Example 6, ethyl 2-{[1-chloro-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetate (0.477 g, 1.03 mmol) was hydrolyzed with potassium hydroxide (0.175 g, 3.12 mmol) in THF (10 mL) and water (10 mL). The title compound was obtained as a light yellow solid (0.249 g), mp 142-143° C. Mass spectrum (+ESI, [M+H]+) m/z 437. 1HNMR (500 MHz, DMSO-d6): δ13.0-13.5 (br, 1H), 8.5 (s, 1H), 8.25 (d, 1H, J=8.7 Hz), 8.1 (d, 1H, J=9.0 Hz), 8.05 (t, 2H, J=10.3 Hz), 7.75 (d,1H, J=8.0 Hz), 7.55 (d, 1H, J=9.2 Hz), 7.4-7.45 (m, 2H), 5.05 (s, 2H), 2.75 (t, 2H, J=7.2 Hz), 1.5-1.6 (m, 2H), 1.1-1.2 (m, 2H), and 0.75 ppm (t, 3H J=7.3 Hz). Elemental Analysis for C25H21ClO5: Calculated: C, 68.73; H, 4.84; N, 0.00. Found: C, 68.56; H, 4.60; N, 0.08.

Sources & evidence

ORD record
ord-b8b2bc19caed48f6b9cde515343ea146
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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