Methyl iodide → Methyl 6-methoxy-2,3-dihydro-benzo[1,4]dioxine

HRID 38382

Reaktionsgleichung

Reaktionsgleichung von HRID 38382
[C:1]([O-:4])([O-])=O.[K+].[K+].[O:7]1[C:12]2[CH:13]=[CH:14][C:15](O)=[CH:16][C:11]=2[O:10][CH2:9][CH2:8]1.I[CH3:19]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CN(C=O)C>[CH3:19][CH:9]1[O:10][C:11]2[CH:16]=[CH:15][C:14]([O:4][CH3:1])=[CH:13][C:12]=2[O:7][CH2:8]1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 91152732,3-Dihydro-1,4-benzodioxin-6-ol

Produkt 1

HCID 21624819Methyl 6-methoxy-2,3-dihydro-benzo[1,4]dioxineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of K2CO3 (47.54 g, 344 mmol) and Bu4NI (1.256 g, 3.4 mmol) in DMF was added 2,3-dihydro-benzo[1,4]dioxin-6-ol (26.2 g, 172 mmol) followed by iodomethane (16.1 ml, 258 mmol). After 16 hours the mixture was filtered. The solution was mixed with H2O and extracted with ethyl acetate. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Purification via flash chromatography (95:5 hexane/ethyl acetate) afforded methyl 6-methoxy-2,3-dihydro-benzo[1,4]dioxine (24.23 g, 85%) as a clear oil.

Aufarbeitung

  1. filtrationAfter 16 hours the mixture was filtered
  2. additionThe solution was mixed with H2O
  3. extractionextracted with ethyl acetate
  4. washThe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification via flash chromatography (95:5 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-88354675dfb54aa5b93c85ab368323b4
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524725B2

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