Sodium hydride → [(R)-2-(2,2-diethoxyethoxy)-4-pentenyloxymethyl]benzene

HRID 217985

Reaktionsgleichung

Reaktionsgleichung von HRID 217985
[CH2:1]([O:8][CH2:9][C@H:10]([OH:14])[CH2:11][CH:12]=[CH2:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:17]([O:19][CH:20]([O:23][CH2:24][CH3:25])[CH2:21]Br)[CH3:18]>CN(C=O)C>[CH2:17]([O:19][CH:20]([O:23][CH2:24][CH3:25])[CH2:21][O:14][C@H:10]([CH2:11][CH:12]=[CH2:13])[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:18]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 10375318(2R)-1-(benzyloxy)pent-4-en-2-ol

Produkt 1

HCID 59281174[(R)-2-(2,2-diethoxyethoxy)-4-pentenyloxymethyl]benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(R)-1-Benzyloxy-4-penten-2-ol (3.13 g) was dissolved in DMF (32 ml), and sodium hydride (60%, 0.91 g) was added in an ice bath. After stirring at the same temperature for 30 minutes, bromoacetaldehyde diethyl acetal (3.03 ml) was added. The mixture was heated to room temperature and stirred for two hours, and then heated to 50° C. and stirred for one hour. After cooling to room temperature, ice was added to the reaction solution. The reaction solution was extracted with ethyl acetate. The organic layer was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound. The mixture containing the recovered raw material was reacted under the same conditions. The title compound was obtained by purification by the same method (total yield: 5.00 g).

Aufarbeitung

  1. stirringstirred for two hours
  2. temperatureheated to 50° C.
  3. stirringstirred for one hour
  4. temperatureAfter cooling to room temperature
  5. additionice was added to the reaction solution
  6. extractionThe reaction solution was extracted with ethyl acetate
  7. washThe organic layer was washed with water and brine
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3667462c2a6245cf8e89e8e792959184
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198269B2

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