Reaktion #52432

ord-706369a3ae8c4f93abc6733ccf08f6a0

Reaktionsgleichung

CCOC(=O)c1ccc(C#Cc2ccc(C3(OCc4ccccc4)CC3)cc2)cc1
ethyl 4-[4-(1-benzyloxycyclopropyl)-phenylethynyl]-benzoate
CCOC(=O)c1ccc(C#Cc2ccc(C3(OCc4ccccc4)CC3)cc2)cc1
Compound 75
CCOC(=O)c1ccc(C#Cc2ccc(C3(OCc4ccccc4)CC3)cc2)cc1
ethyl 4-[4-(1-benzyloxycyclopropyl)-phenylethynyl]-benzoate
[Na+].[OH-]
NaOH
→
O=C(O)c1ccc(C#Cc2ccc(C3(OCc4ccccc4)CC3)cc2)cc1
title compound
Ausbeute 89.0%
O=C(O)c1ccc(C#Cc2ccc(C3(OCc4ccccc4)CC3)cc2)cc1
4-[4-(1-Benzyloxycyclopropyl)-phenylethynyl]-benzoic acid
Ausbeute 89.0%

Edukte

—
aqueous solution
CCOC(=O)c1ccc(C#Cc2ccc(C3(OCc4ccccc4)CC3)cc2)cc1
ethyl 4-[4-(1-benzyloxycyclopropyl)-phenylethynyl]-benzoate
CCOC(=O)c1ccc(C#Cc2ccc(C3(OCc4ccccc4)CC3)cc2)cc1
Compound 75
CCOC(=O)c1ccc(C#Cc2ccc(C3(OCc4ccccc4)CC3)cc2)cc1
ethyl 4-[4-(1-benzyloxycyclopropyl)-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-benzyloxycyclopropyl)-phenylethynyl]-benzoate (Compound 75, 78.0 mg, 0.20 mmol) in ethanol (3 mL) and tetrahydrofuran (3 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 65.0 mg (89%) of the title compound as a solid.

Quelle

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