Reaktion #1731926

Reaktionsgleichung

[4-(4-benzyloxy-benzyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

→

[6-fluoro-4-(4-hydroxy-benzyl)-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

Ausbeute 120.3%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction mixture was then filtered through a bed of celite
2. 2
   EinengenThe filtrate was concentrated

Vorschrift

A round-bottom flask was charged with [4-(4-benzyloxy-benzyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (4.17 g, 9.73 mmol) in ethanol (250 mL). A full spatula scoop of 10% palladium on carbon was added into the reaction flask. The reaction mixture was stirred under hydrogen gas at atmospheric pressure overnight at room temperature. The reaction mixture was then filtered through a bed of celite. The filtrate was concentrated to afford 3.96 g (100%) of [6-fluoro-4-(4-hydroxy-benzyl)-3-methyl-naphthalen-2-yl]-acetic acid methyl ester, which was used in the next step without further purification. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.17 (br. s, 1 H), 7.91 (dd, J=8.7, 6.2 Hz, 1 H), 7.74 (s, 1 H), 7.64 (dd, J=12.2, 1.9 Hz, 1 H), 7.33 (td, J=8.7, 1.9 Hz, 1 H), 6.83 (d, J=8.5 Hz, 2 H), 6.62 (d, J=8.5 Hz, 2 H), 4.32 (s, 2 H), 3.93 (s, 2 H), 3.64 (s, 3 H), 2.30 (s, 3 H).

Quelle