Ethylene Glycol → Methyl 1,4-dioxaspiro[4.5]decane-7-carboxylate

HRID 574980

Reaktionsgleichung

Reaktionsgleichung von HRID 574980
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[CH2:29](O)[CH2:30][OH:31].C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:31]1[C:2]2([CH2:7][CH2:6][CH2:5][CH:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]2)[O:1][CH2:29][CH2:30]1

Komponenten

6

Edukt 4

HCID 174Ethylene GlycolHCID 8471TriethylamineHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 566099Methyl 3-oxocyclohexane-1-carboxylate

Produkt 1

HCID 372311Methyl 1,4-dioxaspiro[4.5]decane-7-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Methyl 3-oxocyclohexanecarboxylate (930 mg) and pyridinium p-toluenesulfonate (299 mg) were combined in toluene (29.8 mL) to give a colorless solution. Ethylene glycol (0.996 mL) was added and the reaction was refluxed under Dean-Stark conditions for 2 days. The reaction was cooled to room temperature, triethylamine was added, and then the mixture was concentrated by rotary evaporation. The residue was purified by regular phase flash column chromatography (Analogix 0-40% hexane/ethyl acetate).

Aufarbeitung

  1. customto give a colorless solution
  2. temperaturethe reaction was refluxed under Dean-Stark conditions for 2 days
  3. concentrationthe mixture was concentrated by rotary evaporation
  4. customThe residue was purified by regular phase flash column chromatography (Analogix 0-40% hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-89ae61a478bb4ddc8bfe5bc0a9a34275
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034875B2

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