Cycloate → 6-Methoxy-1-oxaspiro[2,5]octane

HRID 639552

Reaktionsgleichung

Reaktionsgleichung von HRID 639552
[H-].[Na+].[I-].C[S+](C)(C)=O.[CH3:9][O:10][CH:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1.[CH3:18]CN(C(SCC)=O)C1CCCCC1>CS(C)=O.O>[CH3:9][O:10][CH:11]1[CH2:16][CH2:15][C:14]2([O:17][CH2:18]2)[CH2:13][CH2:12]1

Komponenten

7

Edukt 4

HCID 14337CycloateHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 5350284-Methoxycyclohexanone

Produkt 1

HCID 153294906-Methoxy-1-oxaspiro[2,5]octane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred suspension of sodium hydride (60% in mineral oil, 1.20 g, 30.0 mmol) in dimethylsulfoxide (19 mL) was added trimethylsulfoxonium iodide (6.89 g, 31.3 mmol) at room temperature, and the mixture was stirred at room temperature for 30 min. To this mixture was added a solution of 4-methoxycyclohexanone (3.53 g, 10.0 mmol, prepared according to Shvily, Ronit et al., J. Chem. Soc. Perkin Trans. 2, 1997, 6, 1221) in dimethylsulfoxide (95 mL) dropwise at room temperature, and the mixture was stirred at room temperature for 20 h. Then the mixture was diluted with water (1.0 L), and extracted with diethyl ether (200 mL×6). The combined organic layers were dried over magnesium sulfate, and concentrated in vacuo. The residue was chromatographed on a column of silica gel eluting n-hexane/ethyl acetate (v/v=15/1˜10/1) to give 338 mg (9%, cis) and 204 mg (5%, trans) of the title compound as colorless oil respectively.

Aufarbeitung

  1. customprepared
  2. extractionextracted with diethyl ether (200 mL×6)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on a column of silica gel
  6. washeluting n-hexane/ethyl acetate (v/v=15/1˜10/1)

Quellen und Nachweise

ORD-Eintrag
ord-ea14e95256c9498cae07544686a60796
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691881B2

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