1,4-Cyclohexanedicarboxylic acid → 4-(Methoxycarbonyl)cyclohexane-1-carboxylic acid

HRID 14314

Reaktionsgleichung

Reaktionsgleichung von HRID 14314
[CH:1]1([C:10]([OH:12])=[O:11])[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.O1CCC[CH2:14]1.CO.C[Si](C=[N+]=[N-])(C)C>C(O)(=O)C>[CH3:14][O:8][C:7]([CH:4]1[CH2:3][CH2:2][CH:1]([C:10]([OH:12])=[O:11])[CH2:6][CH2:5]1)=[O:9]

Komponenten

5

Edukt 3

HCID 141061,4-Cyclohexanedicarboxylic acidHCID 167693TrimethylsilyldiazomethaneHCID 21899815MeOH tetrahydrofuran

Produkt 1

HCID 2968504-(Methoxycarbonyl)cyclohexane-1-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-1998172ed4714cdb921ff60d947af049
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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