Tetrahydrofuran → HCID 15614950, Verbindung

Reaktionsgleichung

[F:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:16][CH3:17])[C:8]=2[C:12]([F:15])([F:14])[F:13])[C:3]=1C(O)=O.[CH2:21]([O:23][C:24]([N:26]=[C:27]=NC(C)(C)C)=[O:25])[CH3:22].C1C[O:36]CC1>>[F:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:16][CH3:17])[C:8]=2[C:12]([F:15])([F:14])[F:13])[C:3]=1[C:27]([NH:26][C:24](=[O:25])[O:23][CH2:21][CH3:22])=[O:36]

Komponenten

Edukt 3

HCID 8028Tetrahydrofuran

HCID 13839325HCID 13839325, Verbindung

HCID 15614934HCID 15614934, Verbindung

Produkt 1

HCID 15614950HCID 15614950, Verbindung

Versuchsvorschrift

According to the procedure of O. Mitsunobu et al, Bull. Chem. Soc. Japan, 45, 3607 (1972), a solution of 2-fluoro-6-methoxy-5-(trifluoromethyl)-1-naphthoic acid (2.30 g, 8.00 mmol, prepared by the process of Example 10), and ethoxycarbonyl-t-butylcarbodiimide (1.50 g, 1.1 eq) in anhydrous THF (40 mL) was heated to reflux for 21/2 hours under a dry nitrogen atmosphere. The reaction was cooled to room temperature and the THF was removed. The crude product was triturated with ether to provide the title compound as an off white solid (2.37 g, 82%). A small sample was recrystallized from CHCl3 :petroleum ether for analysis, m.p. 172°-174° C.