Potassium Hydroxide → HCID 10142554, compound

HRID 1359244Notes

Reaction equation

HRID 1359244 reaction equation
C([O:3][C:4](=[O:34])[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)[C:8]=1[Br:33])C.[OH-].[K+]>C1COCC1.O>[Br:33][C:8]1[C:9]2[C:14](=[CH:13][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:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[O:6][CH2:5][C:4]([OH:34])=[O:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 69831236HCID 69831236, compound

Product 1

HCID 10142554HCID 10142554, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure described in Step 4 of Example 6, [1-bromo-6-(5-chloro-3-pentanoyl-benzofuran -2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester (0.25 g, 0.46 mmol) was hydrolyzed with potassium hydroxide (0.300 g, 5.36 mmol) in THF (10 mL) and water (10 mL). Crystallization from ethyl acetate afforded the title compound as an off-white solid (0.21 g), mp 130-132° C. Mass spectrum (−APCl, [M−H]−) m/z 513, 515, 517. 1HNMR (400 MHz, DMSO-d6): δ13.25 (br s,1H), 8.48 (d,1H, J=1.5 Hz), 8.25 (d, 1H, J=9.0 Hz), 8.14 (d, 1H, J=9.0 Hz), 8.04 (d, 1H, J=2.2 Hz), 7.99 (dd, 1H, J=9.0, 1.8 Hz), 7.79 (d, 1H, J=8.8 Hz), 7.52-7.48 (m, 2H), 5.03 (s, 2H), 2.72 (t, 2H, J=7.3 Hz), 1.56-1.48 (m, 2H), 13H, 1.17-1.07 (m, 2H), and 0.70 ppm (t, 3H, J=7.4 Hz). Elemental Analysis for C25H20BrClO5: Calculated: C, 58.22; H, 3.91; N, 0.00. Found: C, 58.24; H, 3.73; N, 0.03.

Workup

  1. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-cdb77e4abda14cb1badb5a5840d19453
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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