Triethylamine → 3-(4-Cyclohexyloxy-phenyl)-2-hydroxy-4-oxo-octanoic acid ethyl ester

HRID 401893

Reaktionsgleichung

Reaktionsgleichung von HRID 401893
[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.[C:28]([O:32][CH2:33][CH3:34])(=[O:31])[CH:29]=[O:30]>C1COCC1>[CH2:33]([O:32][C:28](=[O:31])[CH:29]([OH:30])[CH: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])[CH3:34]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 70211Ethyl oxoacetateHCID 673757361-(4-Cyclohexyloxy-phenyl)hexan-2-one

Produkt 1

HCID 673757473-(4-Cyclohexyloxy-phenyl)-2-hydroxy-4-oxo-octanoic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-(4-cyclohexyloxy-phenyl)-hexan-2-one (86.4 mmol, 23.7 g) and triethylamine (86.4 mmol, 12.1 mL) in THF (10 mL) was added a solution of ethyl glyoxylate (50% in toluene, 432 mmol, 86 mL) and continued stirring for 12 h during which time the starting material was fully consumed as judged by TLC. After removal of volatiles in vacuo, the crude product was purified on a 300 g SiO2 cartridge with 10-15% ethyl acetate in hexanes to afford 3-(4-cyclohexyloxy-phenyl)-2-hydroxy-4-oxo-octanoic acid ethyl ester

Aufarbeitung

  1. customwas fully consumed
  2. customAfter removal of volatiles in vacuo
  3. customthe crude product was purified on a 300 g SiO2 cartridge with 10-15% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ef8c3ce575934601920ac6a1873eb5f1
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741900B2

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