Water → Allyl benzyl ether

HRID 564327

Reaktionsgleichung

Reaktionsgleichung von HRID 564327
[H-].[Na+].[CH2:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.[CH2:12]1C[O:15][CH2:14][CH2:13]1>>[CH2:14]([O:15][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH:13]=[CH2:12]

Komponenten

5

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 24758Sodium hydride

Produkt 1

HCID 84542Allyl benzyl etherAusbeute 53 %

Versuchsvorschrift

To a solution of isomer A product from Step 1 (1.62 g, 4.23 mmol) in THF (50 mL) was added NaH 60% (540 mg, 13.4 mmol) followed by benzylbromide (1.5 mL, 13.4 mmol) and the reaction was stirred at 55 C overnight. The cooled mixture was poured into water, extracted with EtOAc, dried over Na2SO4 and concentrated. The residue was purified by flash-chromatography over silica gel (eluted with Hexanes/AcOEt 99:1 to 50:50) to afford 1.07 g (53%) of allylbenzylether isomer A.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by flash-chromatography over silica gel (eluted with Hexanes/AcOEt 99:1 to 50:50)

Quellen und Nachweise

ORD-Eintrag
ord-7a23ec14645748e2bee58d1eb3ec3865
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067621B2

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