Toluene → N-methoxy-N-methyl-1,4-Dioxaspiro[4.5]decane-8-carboxamide

HRID 626179

Reaktionsgleichung

Reaktionsgleichung von HRID 626179
[CH3:1][O:2][N:3]([CH3:13])[C:4]([CH:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]1)=[O:5].C1(C)C(S([O-])(=O)=[O:21])=CC=CC=1.[C:25]1([CH3:31])C=CC=CC=1>>[CH3:1][O:2][N:3]([CH3:13])[C:4]([CH:6]1[CH2:11][CH2:10][C:9]2([O:21][CH2:25][CH2:31][O:12]2)[CH2:8][CH2:7]1)=[O:5]

Komponenten

4

Edukt 3

HCID 1140TolueneHCID 3424274ToluenesulfonateHCID 89657356N-Methoxy-N-methyl-4-oxocyclohexanecarboxamide

Produkt 1

HCID 15643268N-methoxy-N-methyl-1,4-Dioxaspiro[4.5]decane-8-carboxamideAusbeute 38,4 %

Versuchsvorschrift

A mixture of N-methoxy-N-methyl-4-oxocyclohexanecarboxamide (2.1 g, 0.114 mol), glycol (0.9 g, 0.136 mol) and toluenesulfonate (0.1 g, cat) in toluene (30 mL) was refluxed overnight and then concentrated. Water was added, and the mixture was extracted with ethyl acetate. The extract was concentrated and purified by silica gel column chromatography (CH2Cl2:MeOH=100:1) to give the desired product (1 g, 38.4% yield).

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. concentrationconcentrated
  3. additionWater was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. concentrationThe extract was concentrated
  6. custompurified by silica gel column chromatography (CH2Cl2:MeOH=100:1)

Quellen und Nachweise

ORD-Eintrag
ord-4174fdfc1f764fdbb1f57ec9c09d9ada
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309211B2

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