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

HRID 1936114Notes

Reaction equation

HRID 1936114 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[C:26]([CH3:29])([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[C:26]([CH3:27])([CH3:29])[CH3:28])[CH2:6][CH2:5]1)[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22568931HCID 22568931, compound2×

Product 1

HCID 102700304-[4-(1-Ethoxycyclopropyl)-3-tert-butyl-phenylethynyl]-benzoic acidYield 62%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure I; a solution of ethyl 4-[4-(1-ethoxycyclopropyl)-3-tert-butyl-phenylethynyl]-benzoate (Compound 103, 70.0 mg, 0.18 mmol) in ethanol (3 mL) and tetrahydrofuran (3 mL) was treated with NaOH (240.0 mg, 6.0 mmols, 3.0 mL of a 2N aqueous solution) and stirred overnight at room temperature. Work-up afforded 40 mg (62%) the title compound as a pale-yellow solid.

Sources & evidence

ORD record
ord-fb3754b05aec4817b64b2c3e0d800437
Source dataset
uspto-grants-2002_05
Patent number
US06387951B1

Reaction notes

Loading…