Benzyl Bromide → (R)-5-Benzyloxymethyl-dihydro-furan-2-one

HRID 8198

Reaktionsgleichung

Reaktionsgleichung von HRID 8198
[OH:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[CH2:5][CH2:4]1.[H-].[Na+].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH2:11]([O:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[CH2:5][CH2:4]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

7

Edukt 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 6950353(5R)-Dihydro-5-(hydroxymethyl)-2(3H)-furanone

Produkt 1

HCID 11084999(R)-5-Benzyloxymethyl-dihydro-furan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (R)-5-hydroxymethyl-dihydro-furan-2-one (5 g, 43.06 mmol) in tetrahydrofuran (130 mL) is added sodium hydride (2.58 g, 60% oil dispersion, 64.59 mmol) and tetrabutylammonium iodide (spatula) and stirred for 30 min. To the mixture is added benzyl bromide (6.18 mL, 51.67 mmol) and refluxed for 3 h. The mixture is cooled and diluted with ethyl acetate (150 mL), washed with a saturated solution of ammonium chloride (150 mL) and brine. The mixture is dried over magnesium sulfate, filtered and concentrated in vacuo to yield the title compound, 8.87 g (100%), as a pale yellow oil.

Aufarbeitung

  1. temperaturerefluxed for 3 h
  2. temperatureThe mixture is cooled
  3. washwashed with a saturated solution of ammonium chloride (150 mL) and brine
  4. dry with materialThe mixture is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b1c79f3c05474aeeb8f26acb075fcc5f
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087626B2

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