Acetone → (R)-6-Cyclohexyl-4-methyl-hexanal

HRID 132629

Reaktionsgleichung

Reaktionsgleichung von HRID 132629
[CH:1]1([CH2:7][CH2:8][C@@H:9]([CH3:17])[CH2:10][CH2:11][CH:12]2[O:14]C2(C)C)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(C)=O.I([O-])(=O)(=O)=O.[K+]>O>[CH:1]1([CH2:7][CH2:8][C@@H:9]([CH3:17])[CH2:10][CH2:11][CH:12]=[O:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 516896Potassium periodateHCID 865979603-((R)-5-Cyclohexyl-3-methyl-pentyl)-2,2-dimethyl-oxirane

Produkt 1

HCID 86597961(R)-6-Cyclohexyl-4-methyl-hexanalAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A flask was charged with 10.65 g (44.7 mmol) of 3-((R)-5-cyclohexyl-3-methyl-pentyl)-2,2-dimethyl-oxirane, 70 mL of acetone, 12.3 g (53.6 mmol) of potassium periodate, 70 mL of water, and 0.765 g (4 mmol) of tosic acid-monohydrate. The mixture was stirred for 46 hours. The acetone was removed under reduced pressure, and the mixture was diluted with water. The aqueous layer was extracted with hexanes and dried with sodium sulfate. The drying agent was filtered off and solvent was removed under reduced pressure to get 7.12 g (81% yield) of a clear oil: 1H NMR (400 MHz, CDCl3) ppm 0.87 (m, 5H) 1.13 (m, 3H) 1.25 (m, 5H) 1.66 (m, 8H) 2.40 (m, 2H) 9.75 (s, 1H). MS (APCI) m+1/z is inconclusive.

Aufarbeitung

  1. customThe acetone was removed under reduced pressure
  2. additionthe mixture was diluted with water
  3. extractionThe aqueous layer was extracted with hexanes
  4. dry with materialdried with sodium sulfate
  5. filtrationThe drying agent was filtered off
  6. customsolvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6b8f5bed32b24deb870c583f9c4eceee
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388023B2

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