Reaktion #52445

ord-789b75903f614f679e6c47dfea6ce2df

Reaktionsgleichung

CCOC(=O)c1ccc(C#Cc2ccc(C3(OC(C)C)CC3)c(C)c2)cc1
ethyl 4-[4-(1-isopropoxycyclopropyl)-3-methyl-phenylethynyl]-benzoate
CCOC(=O)c1ccc(C#Cc2ccc(C3(OC(C)C)CC3)c(C)c2)cc1
Compound 83
CCOC(=O)c1ccc(C#Cc2ccc(C3(OC(C)C)CC3)c(C)c2)cc1
ethyl 4-[4-(1-isopropoxycyclopropyl)-3-methyl-phenylethynyl]-benzoate
[Na+].[OH-]
NaOH
→
Cc1cc(C#Cc2ccc(C(=O)O)cc2)ccc1C1(OC(C)C)CC1
title compound
Ausbeute 69.0%
Cc1cc(C#Cc2ccc(C(=O)O)cc2)ccc1C1(OC(C)C)CC1
4-[4-(1-Isopropoxycyclopropyl)-3-methyl-phenylethynyl]-benzoic acid
Ausbeute 69.0%

Edukte

—
aqueous solution
CCOC(=O)c1ccc(C#Cc2ccc(C3(OC(C)C)CC3)c(C)c2)cc1
ethyl 4-[4-(1-isopropoxycyclopropyl)-3-methyl-phenylethynyl]-benzoate
CCOC(=O)c1ccc(C#Cc2ccc(C3(OC(C)C)CC3)c(C)c2)cc1
Compound 83
CCOC(=O)c1ccc(C#Cc2ccc(C3(OC(C)C)CC3)c(C)c2)cc1
ethyl 4-[4-(1-isopropoxycyclopropyl)-3-methyl-phenylethynyl]-benzoate
[Na+].[OH-]
NaOH

Reagenzien

Keine

Lösungsmittel

CCO
ethanol
C1CCOC1
tetrahydrofuran

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Using General Procedure I; a solution of ethyl 4-[4-(1-isopropoxycyclopropyl)-3-methyl-phenylethynyl]-benzoate (Compound 83, 60.0 mg, 0.17 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 38.0 mg (69%) of the title compound as a colorless solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06855512B2uspto-grants-2005_02