Sodium Hydroxide → 4-[4-(1-Ethoxycyclopropyl)-3-isopropyl-phenylethynyl]-benzoic acid

HRID 1935896Notes

Reaction equation

HRID 1935896 reaction equation
[CH2:1]([O:3][C:4]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21]CC)=[O:20])=[CH:17][CH:16]=3)=[CH:9][C:8]=2[CH:26]([CH3:28])[CH3:27])[CH2:6][CH2:5]1)[CH3:2].[OH-].[Na+]>C(O)C.O1CCCC1>[CH2:1]([O:3][C:4]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]3[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:24][CH:25]=3)=[CH:9][C:8]=2[CH:26]([CH3:27])[CH3:28])[CH2:6][CH2:5]1)[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22568977HCID 22568977, compound2×

Product 1

HCID 225688544-[4-(1-Ethoxycyclopropyl)-3-isopropyl-phenylethynyl]-benzoic acidYield 98.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure I; A solution of ethyl 4-[4-(1-ethoxycyclopropyl)-3-isopropyl-phenylethynyl]-benzoate (Compound 99, 28.0 mg, 0.07 mmol) in ethanol (2 mL) and tetrahydrofuran (2 mL) was treated with NaOH (80.0 mg, 2.0 mmols, 2.0 mL of a 1N aqueous solution) and stirred overnight at room temperature. Work-up afforded 24 mg (92%) the title compound as a pale-yellow solid.

Sources & evidence

ORD record
ord-e9c32febf9ab4d9a888d91770398af3e
Source dataset
uspto-grants-2002_05
Patent number
US06387892B1

Reaction notes

Loading…