Triethylamine → 5-(5-Fluoro-2-methoxyphenyl)-3-hydroxy-5-methyl-3-(trifluoromethyl)hexan-2-one

HRID 2055027Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2055027
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH3:22])=[C:6]([C:8]([CH3:20])([CH3:19])[CH2:9][C:10]([C:15]([F:18])([F:17])[F:16])([OH:14])[CH:11]([OH:13])[CH3:12])[CH:7]=1.C(N(CC)CC)C.[Cl-].[NH4+]>CS(C)=O.C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH3:22])=[C:6]([C:8]([CH3:19])([CH3:20])[CH2:9][C:10]([OH:14])([C:15]([F:18])([F:17])[F:16])[C:11](=[O:13])[CH3:12])[CH:7]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 219488565-(5-Fluoro-2-methoxyphenyl)-5-methyl-3-(trifluoromethyl)hexane-2,3-diol

Produkt 1

HCID 219488285-(5-Fluoro-2-methoxyphenyl)-3-hydroxy-5-methyl-3-(trifluoromethyl)hexan-2-oneAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.46 g (4.5 mmol) of 5-(5-fluoro-2-methoxyphenyl)-5-methyl-3-(trifluoromethyl)hexane-2,3-diol and 3.14 ml (22.5 mmol) of triethylamine in 16.3 ml of DMSO and 50 ml of methylene chloride are mixed in portions with 4.3 g (27 mmol) of pyridine-sulfur trioxide complex at room temperature. After 20 hours at room temperature, it is hydrolyzed with saturated ammonium chloride solution while being cooled with ice and extracted with diethyl ether. The combined extracts are dried (sodium sulfate) and concentrated by evaporation. Column chromatography on silica gel with hexane-ethyl acetate yields 1.04 g of the product.

Aufarbeitung

  1. temperaturewhile being cooled with ice
  2. extractionextracted with diethyl ether
  3. dry with materialThe combined extracts are dried (sodium sulfate)
  4. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-7a20e7f927d7470db6b91ecfcc1e9a64
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07329753B2

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