Ethyl oxoacetate → 3-(3-Bromo-4-cyclohexyloxy-phenyl)-2-hydroxy-4-oxo-octanoic acid ethyl ester

HRID 402003Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 402003
[Br:1][C:2]1[CH:3]=[C:4]([CH2:15][C:16](=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20])[CH:5]=[CH:6][C:7]=1[O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[CH2:22]([O:24][C:25](=[O:28])[CH:26]=[O:27])[CH3:23]>C1(C)C=CC=CC=1.C(N(CC)CC)C.C(Cl)Cl>[CH2:22]([O:24][C:25](=[O:28])[CH:26]([OH:27])[CH:15]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[C:2]([Br:1])[CH:3]=1)[C:16](=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20])[CH3:23]

Komponenten

6

Edukt 2

HCID 70211Ethyl oxoacetateHCID 673736281-(3-Bromo-4-cyclohexyloxy-phenyl)-hexan-2-one

Produkt 1

HCID 673752833-(3-Bromo-4-cyclohexyloxy-phenyl)-2-hydroxy-4-oxo-octanoic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 1-(3-Bromo-4-cyclohexyloxy-phenyl)-hexan-2-one (7.08 mmol, 2.5 g), oxo-acetic acid ethyl ester solution in toluene (2.8 mL, 50% solution in toluene) and triethylamine (0.5 mL) was stirred at ambient temperature for 16 h. The reaction mixture was diluted with DCM (300 mL), washed with water (3×100 mL), dried the organic layer and concentrated under reduced pressure. The resultant residue was purified by flash silica gel chromatography using mixture of hexanes in ethyl acetate (9:1) to provide 3-(3-bromo-4-cyclohexyloxy-phenyl)-2-hydroxy-4-oxo-octanoic acid ethyl ester (2.0 g).

Aufarbeitung

  1. washwashed with water (3×100 mL)
  2. customdried the organic layer
  3. concentrationconcentrated under reduced pressure
  4. customThe resultant residue was purified by flash silica gel chromatography
  5. additionmixture of hexanes in ethyl acetate (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-3f0e28688d4b4c4080e09a7a0e3f0c89
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741900B2

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