Benzyl Bromide → HCID 86672616, Verbindung

HRID 470714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 470714
[H-].[Na+].[CH3:3][O:4][C:5]1([O:16][CH3:17])[CH2:15][C:7]2([CH2:10][C:9]([CH2:13][OH:14])([CH2:11][OH:12])[CH2:8]2)[CH2:6]1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+]>O1CCCC1.CN(C)C=O>[CH2:18]([O:14][CH2:13][C:9]1([CH2:11][O:12][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:8][C:7]2([CH2:6][C:5]([O:4][CH3:3])([O:16][CH3:17])[CH2:15]2)[CH2:10]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

7

Edukt 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 68309438HCID 68309438, Verbindung

Produkt 1

HCID 86672616HCID 86672616, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium hydride (755 mg, 17.3 mmol) was added to a dimethylformamide (40 ml)/tetrahydrofuran (20 ml) solution of the compound (1.56 g, 7.20 mmol) obtained in Step 1 above under ice cooling, the resulting mixture was stirred at room temperature for 10 minutes, then benzyl bromide (2.06 ml, 17.3 mmol) was added and the resulting mixture was stirred for 24 hours. Saturated ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography [n-hexane:ethyl acetate=4:1 (v/v)] to give 2.25 g (79%) of the title compound as an oil.

Aufarbeitung

  1. stirringthe resulting mixture was stirred for 24 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography [n-hexane:ethyl acetate=4:1 (v/v)]

Quellen und Nachweise

ORD-Eintrag
ord-b46e6a1895c04ccfb7c4ffd4f1291c19
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629133B2

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