Trifluoroacetic acid → 4-(5-Bromo-3-methylpyridin-2-yl)-4-hydroxycyclohexanone

HRID 1748528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748528
FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:10]=[C:11]([CH3:26])[C:12]([C:15]2([OH:25])[CH2:24][CH2:23][C:18]3(OCC[O:19]3)[CH2:17][CH2:16]2)=[N:13][CH:14]=1.[OH-].[Na+]>O>[Br:8][C:9]1[CH:10]=[C:11]([CH3:26])[C:12]([C:15]2([OH:25])[CH2:16][CH2:17][C:18](=[O:19])[CH2:23][CH2:24]2)=[N:13][CH:14]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 866924748-(5-Bromo-3-methylpyridin-2-yl)-1,4-dioxaspiro[4,5]decan-8-ol

Produkt 1

HCID 866924774-(5-Bromo-3-methylpyridin-2-yl)-4-hydroxycyclohexanoneAusbeute 41,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

Trifluoroacetic acid (11 ml) and water (1 ml) were added to 8-(5-bromo-3-methylpyridin-2-yl)-1,4-dioxaspiro[4,5]decan-8-ol (7.45 g) described in Reference Example 105(1) and stirred at room temperature. After completion of the reaction, water was added and neutralized by the addition of 1N aqueous solution of sodium hydroxide and extracted with chloroform. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine successively, dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 4-(5-bromo-3-methylpyridin-2-yl)-4-hydroxy-cyclohexanone (2.69 g) as a white solid.

Aufarbeitung

  1. additionwas added
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-5e63ee9959fd4148941415772d062957
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150555B2

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