Benzyl Bromide → HCID 178501330, Verbindung

HRID 217234Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 217234
[CH3:1][O:2][C:3]([CH:5]1[CH2:8][CH:7]([OH:9])[CH2:6]1)=[O:4].[H-].[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[CH3:1][O:2][C:3]([C@H:5]1[CH2:8][C@H:7]([O:9][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6]1)=[O:4]

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 12815112Cyclobutanecarboxylic acid, 3-hydroxy-, methyl ester

Produkt 1

HCID 178501330HCID 178501330, VerbindungAusbeute 15,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of cis-trans mixture of 3-hydroxy-cyclobutanecarboxylic acid methyl ester (1.30 g, 10 mmol) in DMF 13 mL, NaH (50% in oil, 720 mg, 15 mmol) is added at 0° C. After stirring at 0° C. for 15 minutes, benzyl bromide (1.43 ml, 12 mmol) is added at 0° C. The mixture is stirred at room temperature for 2 hours and quenched with H2O. The solution is extracted with AcOEt. The organic layer is washed with H2O and brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give trans-3-benzyloxy-cyclobutanecarboxylic acid methyl ester (340 mg, 15.4%); TLC (hexane/AcOEt, 5:1) Rf 0.40, 1H NMR (400 MHz, chloroform-d) ppm 2.26-2.34 (m, 2H), 2.48-2.52 (m, 2H), 3.02-3.06 (m, 1H), 3.69 (s, 3H), 4.26-4.33 (m, 1H), 4.42 (s, 2H), 7.27-7.35 (m, 5H).

Aufarbeitung

  1. additionis added at 0° C
  2. stirringThe mixture is stirred at room temperature for 2 hours
  3. customquenched with H2O
  4. extractionThe solution is extracted with AcOEt
  5. washThe organic layer is washed with H2O and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b29af3b0b60948b080eed8edcd26dff2
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193349B2

Notizen zur Reaktion

Wird geladen…