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

HRID 2165790

Reaktionsgleichung

Reaktionsgleichung von HRID 2165790
[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 0.15 M 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-ae2386b1a2604242bae028d3fbeed639
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04940797

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