Water → 8-Methoxy-8-phenyl-1,4-dioxaspiro[4.5]decane

HRID 1816348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1816348
[C:1]1([C:7]2([OH:17])[CH2:16][CH2:15][C:10]3([O:14][CH2:13][CH2:12][O:11]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[CH3:19].[H-].[Na+].O>CN(C)C=O.CCOCC>[CH3:19][O:17][C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:16][CH2:15][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:9][CH2:8]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 149775528-Phenyl-1,4-dioxaspiro[4.5]decan-8-ol

Produkt 1

HCID 224929828-Methoxy-8-phenyl-1,4-dioxaspiro[4.5]decane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 8-phenyl-1,4-dioxaspiro[4.5]decan-8-ol (5.76 g) and iodomethane (4.59 ml) in N,N-dimethylformamide (58 ml) was added sodium hydride (60% dispersion in mineral oil) (1.97 g) at 0° C. The solution was stirred for 2 hours at 0° C. and at room temperature for 7.5 hours. The reaction mixture was added to a mixture of water and ether. The organic layer was washed with brine and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (5:1 hexane-ethyl acetate elution) to give 8-methoxy-8-phenyl-1,4-dioxaspiro[4.5]decane (5.968 g).

Aufarbeitung

  1. washThe organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe magnesium sulfate was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (5:1 hexane-ethyl acetate elution)

Quellen und Nachweise

ORD-Eintrag
ord-182e411140474c0b8866c5e6f4d12c8e
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06884774B2

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