Benzyl Bromide → HCID 12827154, Verbindung

HRID 1485836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1485836
[CH:1]1([OH:8])[CH2:6][CH2:5][CH:4]([OH:7])[CH:3]=[CH:2]1.[H-].[Na+].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C=O)C>[CH2:11]([O:7][CH:4]1[CH2:5][CH2:6][CH:1]([OH:8])[CH:2]=[CH:3]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 5508252-Cyclohexene-1,4-diol

Produkt 1

HCID 12827154HCID 12827154, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 34 (79 mg, 0.69 mmol) in DMF (1 mL) was added sodium hydride (14 mg, 0.62 mmol) at 0° C. Benzyl bromide (73 μL, 0.62 mmol) was added to the mixture dropwise, under an argon atmosphere. The reaction was stirred for 16 h at room temperature. Upon completion, distilled water (3 mL) was added to the mixture and the organic layer extracted into ethyl acetate. The organic layers were combined, dried and concentrated to give a crude mixture that was purified by column chromatography (Silica gel, 10%-20% EtOAc in hexane) to give 35 as an oil.

Aufarbeitung

  1. distillationUpon completion, distilled water (3 mL)
  2. additionwas added to the mixture
  3. extractionthe organic layer extracted into ethyl acetate
  4. customdried
  5. concentrationconcentrated
  6. customto give a crude mixture that
  7. customwas purified by column chromatography (Silica gel, 10%-20% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ec927e1369724cf0bc30af60a8959100
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422320B2

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