Sodium borohydride → 2-[3-(3-Bromo-phenyl)-cyclobutyl]-ethanol

HRID 2240964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2240964
C([O:3][C:4](=O)[CH:5]=[C:6]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[CH:11]=2)[CH2:7]1)C.[BH4-].[Na+]>>[Br:16][C:12]1[CH:11]=[C:10]([CH:8]2[CH2:7][CH:6]([CH2:5][CH2:4][OH:3])[CH2:9]2)[CH:15]=[CH:14][CH:13]=1

Komponenten

3

Edukt 2

HCID 4311764Sodium borohydrideHCID 59790338HCID 59790338, Verbindung

Produkt 1

HCID 593052992-[3-(3-Bromo-phenyl)-cyclobutyl]-ethanolAusbeute 30,3 %

Reaktionsbedingungen

Temperatur
67 °C

Versuchsvorschrift

[3-(3-Bromo-phenyl)-cyclobutylidene]-acetic acid ethyl ester (1.96 gm, 6.63 mmol) was suspended in poly(ethylene glycol) (Average MW 400, 40 mL) and sodium borohydride (1.00 g, 26.4 mmol) was added portionwise. The slurry was warmed at 67° C. overnight, then cooled to room temperature and partitioned between 2N hydrochloric acid and diethylether. The ether extracts were dried with sodium sulfate and purified by column chromatography (50% EtOAc/hexanes) to afford 512 mg of an oil (30%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.19-1.29 (m, 1H) 1.31-1.38 (m, 1H) 1.47-1.52 (m, 1H) 1.59-1.68 (m, 1H) 1.97-2.32 (m, 2H) 2.34-2.41 (m, 1H) 4.22-4.31 (m, 1H) 3.23-3.39 (m, 3H) 7.15-7.24 (m, 2H) 7.29-7.38 (m, 2H); MS (EI) m/z 254 [M+·].

Aufarbeitung

  1. temperaturecooled to room temperature
  2. custompartitioned between 2N hydrochloric acid and diethylether
  3. dry with materialThe ether extracts were dried with sodium sulfate
  4. custompurified by column chromatography (50% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ebc501d47dd944d59cd0e8c760aad825
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723368B2

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