Potassium Hydroxide → HCID 10274745, compound

HRID 1359246Notes

Reaction equation

HRID 1359246 reaction equation
C([O:3][C:4](=[O:33])[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:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:20]=4[C:21]=3[C:22](=[O:27])[CH2:23][CH2:24][CH2:25][CH3:26])[CH:13]=2)[CH:8]=1)C.[OH-].[K+]>C1COCC1.O>[Cl:32][C:29]1[CH:30]=[CH:31][C:19]2[O:18][C:17]([C:12]3[CH:13]=[C:14]4[C:9](=[CH:10][CH:11]=3)[CH:8]=[C:7]([O:6][CH2:5][C:4]([OH:33])=[O:3])[CH:16]=[CH:15]4)=[C:21]([C:22](=[O:27])[CH2:23][CH2:24][CH2:25][CH3:26])[C:20]=2[CH:28]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 69830141HCID 69830141, compound

Product 1

HCID 10274745HCID 10274745, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure described in Step 4 of Example 6, [6-(5-chloro-3-pentanoyl-benzofuran-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester (0.26 g, 0. mmol) was hydrolyzed with potassium hydroxide (0.300 g, 5.36 mmol) in THF (20 mL) and water (10 mL). Crystallization from ethyl acetate afforded the title compound as an off-white solid (0.22 g), mp 158-160° C. Mass spectrum (−APCl, [M−H]−) m/z 435, 437. 1HNMR (400 MHz, DMSO-d6): δ13.14 (br s, 1H), 8.37 (d, 1H, J=1.2 Hz), 8.03-8.01 (m, 2 H), 7.97 (d, 1H, J=8.5 Hz), 7.81 (dd, 1H, J=8.3, 1.7 Hz), 7.77 (d, 1H, J=8.8 Hz), 7.48 (dd, 1H, J=8.8, 2.2 Hz), 7.40 (d, 1H, J=2.7 Hz), 7.32 (dd, 1H, J=9.0, 2.5 Hz), 4.85 (s, 2H), 2.69 (t, 2H, J=7.3 Hz), 1.55-1.48 (m, 2H), 1.13-1.05 (m, 2H), and 0.69 ppm (t, 3H, J=7.4 Hz). Elemental Analysis for C25H21ClO5.0.4H2O: Calculated: C, 67.61; H, 4.95; N, 0.00. Found: C, 67.51; H, 4.66; N, 0.05.

Workup

  1. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-09678d49b0c9428ca0d82b68312e82d6
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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