Potassium Hydroxide → HCID 10274166, compound

HRID 1359212Notes

Reaction equation

HRID 1359212 reaction equation
[CH:1]1([CH2:6][C:7]([C:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][C:10]=2[C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[C:23]([O:28][CH2:29][C:30]([O:32]CC)=[O:31])[CH:22]=[CH:21]3)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+]>C1COCC1.O>[CH:1]1([CH2:6][C:7]([C:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][C:10]=2[C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[C:23]([O:28][CH2:29][C:30]([OH:32])=[O:31])[CH:22]=[CH:21]3)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 12082834HCID 12082834, compound

Product 1

HCID 10274166HCID 10274166, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure described in Step 4 of Example 6, ethyl 2-({6-[3-(2-cyclopentylacetyl)-1-benzofuran-2-yl]-2-naphthyl}oxy)acetate (0.324 g, 0.710 mmol), was hydrolyzed with potassium hydroxide (0.120 g, 2.14 mmol) in THF (5 mL) and water (5 mL). Crystallization from acetonitrile yielded the title compound as a cream-colored solid (0.179 g), mp 177-178° C. Mass spectrum (−ESI, [M−H]−) m/z 427; 1HNMR (500 MHz, DMSO-d6): δ12.9-13.4 (br s, 1H), 8.35 (d, 1H, J=1.1 Hz), 7.95-8.05 (m, 3H), 7.8 (dd, 1H, J=8.5 and 1.8 Hz), 7.7 (d, 1H, J=7.6 Hz), 7.4-7.45 (m, 3H), 7.3 (dd, 1H, J=8.9 Hz and 2.5 Hz), 4.85 (s, 2H), 2.75 (d, 2H, J=7.0 Hz), 2.15-2.25 (m, 1H), 1.6-1.65 (m, 2H), 1.35-1.45 (m, 4H), and 0.95-1.0 ppm (m, 2H). Elemental Analysis for C27H24O5: Calculated: C, 75.68; H, 5.65; N, 0.00. Found: C, 75.38; H, 5.46; N, 0.02.

Workup

  1. customCrystallization from acetonitrile

Sources & evidence

ORD record
ord-ae42ac3c688d40519dbc4a38f869ffbd
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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