Water → Methyl 1-(2-oxoethyl)cyclohexanecarboxylate

HRID 2223838

Reaktionsgleichung

Reaktionsgleichung von HRID 2223838
[CH2:1]([C:4]1([C:10]([O:12][CH3:13])=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[CH:2]=C.I(O)(=O)(=O)=[O:15].[Na].O>O1CCCC1.[Os](=O)(=O)(=O)=O>[CH:2]([CH2:1][C:4]1([C:10]([O:12][CH3:13])=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)=[O:15]

Komponenten

6

Edukt 3

HCID 962WaterHCID 10932067Methyl 1-allylcyclohexanecarboxylateHCID 45051826Sodium periodic acid

Produkt 1

HCID 23021124Methyl 1-(2-oxoethyl)cyclohexanecarboxylateAusbeute 72,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 1-allylcyclohexanecarboxylate (340 mg) in tetrahydrofuran (7 mL) were added an aqueous solution of sodium periodic acid (3.4 g, 16.0 mmol) and osmium tetraoxide (100 mg) successively under ice cooling. The solution was stirred at room temperature for 20 hours. Water was added to the reaction solution and insolubles were filtered off. The filtrate was extracted with ethyl acetate, and it was washed in turn with water, sodium thiosulfate and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (250 mg). This product was subjected to the subsequent step without further purification.

Aufarbeitung

  1. filtrationwere filtered off
  2. extractionThe filtrate was extracted with ethyl acetate, and it
  3. washwas washed in turn with water, sodium thiosulfate and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d8e8e350db70403abb1b98193fd99053
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07375115B2

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