Triethylamine → 4-(5-Bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal

HRID 1443165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1443165
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10]([OH:17])([C:13]([F:16])([F:15])[F:14])[CH2:11][OH:12])[CH:7]=1.C(N(CC)CC)C.[Cl-].[NH4+].C(OC)(C)(C)C>ClCCl.CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10]([OH:17])([C:13]([F:16])([F:15])[F:14])[CH:11]=[O:12])[CH:7]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 25517Ammonium ChlorideHCID 179891794-(5-Bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentan-1-ol

Produkt 1

HCID 179891754-(5-Bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanalAusbeute 79,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.13 g (3.06 mmol) of 4-(5-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentan-1-ol is added in 20 ml of dichloromethane and 5.4 ml of DMSO. After mixing with 1.55 g (15.32 mmol) of triethylamine and 975.28 mg (6.13 mmol) of SO3/pyridine complex, the batch is stirred overnight at room temperature. After TLC, another spatula tip full of SO3/pyridine complex is added, and it is further stirred for several hours. The reaction mixture is mixed with saturated ammonium chloride solution and shaken out three times with methyl tert-butyl ether. The combined organic extracts are washed with water and brine. After the solvent is dried and spun off, the residue is chromatographed on a Flashmaster. 902.7 mg (79.81%) of the desired aldehyde (together with the Desbrom compound) is isolated.

Aufarbeitung

  1. additionAfter TLC, another spatula tip full of SO3/pyridine complex is added
  2. stirringit is further stirred for several hours
  3. washThe combined organic extracts are washed with water and brine
  4. customAfter the solvent is dried
  5. customthe residue is chromatographed on a Flashmaster

Quellen und Nachweise

ORD-Eintrag
ord-85112297c2ac4f9497c05d1929ad983f
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659297B2

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