Potassium periodate → (R)-4-Benzyloxy-3-methylbutanal

HRID 466267

Reaktionsgleichung

Reaktionsgleichung von HRID 466267
[CH3:1][CH:2]([CH2:12][CH:13]=C)[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.I([O-])(=O)(=O)=[O:16].[K+]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[CH2:5]([O:4][CH2:3][C@H:2]([CH3:1])[CH2:12][CH:13]=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

6

Edukt 2

HCID 516896Potassium periodateHCID 14608667{[(2-Methylpent-4-EN-1-YL)oxy]methyl}benzene

Produkt 1

HCID 11116875(R)-4-Benzyloxy-3-methylbutanalAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A 250 mL round-bottomed flask, equipped with a magnetic stirring bar and a thermometer was fitted with a septum and a nitrogen inlet. The apparatus was charged with benzyl 2-methyl-4-penten-1-yl ether (2.39 g, 12.5 mmol) in 75 mL of acetone and 25 mL of water. Osmium tetroxide (0.833 mL of an 0.15M aqueous solution, 0.125 mmol) was added in one portion, followed by potassium periodate (6.04 g, 26.2 mmol) in three equal portions. The resulting slurry was stirred for 6 hours at room temperature and decanted into a 500 mL separatory funnel. The aqueous layer was extracted with 3×200 mL of diethyl ether. Each washing was stirred over the solids for 5 minutes, washed with 150 mL of saturated aqueous sodium thiosulfate and 100 mL of saturated aqueous sodium chloride. The combined organic layers were dried over sodium sulfate, filtered, concentrated and chromatographed (4×20 cm column; 4:1 hexane:ethyl acetate) to afford 1.94 g (81%) of aldehyde 4 as a colorless oil. Rf =0.37 (4:1 hexane:ethyl acetate).

Aufarbeitung

  1. customA 250 mL round-bottomed flask, equipped with a magnetic stirring bar
  2. customa thermometer was fitted with a septum and a nitrogen inlet
  3. customdecanted into a 500 mL separatory funnel
  4. extractionThe aqueous layer was extracted with 3×200 mL of diethyl ether
  5. stirringEach washing was stirred over the solids for 5 minutes
  6. washwashed with 150 mL of saturated aqueous sodium thiosulfate and 100 mL of saturated aqueous sodium chloride
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customchromatographed (4×20 cm column; 4:1 hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-32bef3fdc944401e9dfafddf455ae440
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05155228

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