Reaktion #42592

Reaktionsgleichung

trimethylsilyl diazomethane

cyclohexane-1,4-dicarboxylic acid

tetrahydrofuran methanol

→

4-(methoxycarbonyl)cyclohexanecarboxylic acid

Lösungsmittel

—

hexanes

Acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solvent was removed under reduced pressure
2. 2
   SonstigePurification by flash column chromatography (silica, 10:1:0.01 hexanes/ethyl acetate/acetic acid)

Vorschrift

To an ice-cold, stirred solution of cyclohexane-1,4-dicarboxylic acid (3.0 g, 17 mmol) in a mixture of 2:1 tetrahydrofuran/methanol (24 mL) was added trimethylsilyl diazomethane (9 mL of a 2.0 M in hexanes, 18 mmol). The reaction mixture was stirred at room temperature for 2 h. Acetic acid (5 mL) was added and the solvent was removed under reduced pressure. Purification by flash column chromatography (silica, 10:1:0.01 hexanes/ethyl acetate/acetic acid) provided 4-(methoxycarbonyl)cyclohexanecarboxylic acid (1.00 g): 1H NMR (300 MHz, CDCl3) δ 3.68 (s, 3H), 2.53-2.47 (m, 2H), 1.97-1.89 (m, 4H), 1.74-1.66 (m, 4H).

Quelle