Triethylamine → 3-(4-Cyclohexyloxy-phenyl)-4-oxo-2-trifluoromethyl-oct-2-enoic acid methyl ester

HRID 401971

Reaktionsgleichung

Reaktionsgleichung von HRID 401971
[CH:1]1([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15](=[O:20])[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:28][O:29][C:30](=[O:37])[C:31](=O)[C:32]([F:35])([F:34])[F:33]>C1COCC1>[CH3:28][O:29][C:30](=[O:37])[C:31]([C:32]([F:35])([F:34])[F:33])=[C:14]([C:11]1[CH:10]=[CH:9][C:8]([O:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:13][CH:12]=1)[C:15](=[O:20])[CH2:16][CH2:17][CH2:18][CH3:19]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2734931Methyl 3,3,3-trifluoro-2-oxopropanoateHCID 673757361-(4-Cyclohexyloxy-phenyl)hexan-2-one

Produkt 1

HCID 673732163-(4-Cyclohexyloxy-phenyl)-4-oxo-2-trifluoromethyl-oct-2-enoic acid methyl esterAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-(4-cyclohexyloxy-phenyl)-hexan-2-one (Example 14, 4.46 mmol, 1.22 g) and triethylamine (4.46 mmol, 0.62 mL) in THF (5 mL) was added a solution of 3,3,3-trifluoro-2-oxo-propionic acid methyl ester (13.4 mmol, 2.09 g) and continued stirring for 12 h at room temperature. After removal of volatiles in vacuo, the crude product was purified on a 40 g SiO2 cartridge with ethyl acetate/hexanes gradient to afford 3-(4-cyclohexyloxy-phenyl)-4-oxo-2-trifluoromethyl-oct-2-enoic acid methyl ester (1.4 g).

Aufarbeitung

  1. customAfter removal of volatiles in vacuo
  2. customthe crude product was purified on a 40 g SiO2 cartridge with ethyl acetate/hexanes gradient

Quellen und Nachweise

ORD-Eintrag
ord-5ef9159a9aef4e99a7ff89235e0b5dfb
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741900B2

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