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

HRID 2240960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2240960
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 52 %

Reaktionsbedingungen

Temperatur
67 °C

Versuchsvorschrift

[3-(3-Bromo-phenyl)-cyclobutylidene]-acetic acid ethyl ester (1.3 g, 4.48 mmol) was suspended in poly(ethylene glycol) (Average MW 400, 15 mL) and sodium borohydride (650 mg, 17.2 mmol) was added portionwise. The slurry was warmed to 67° C. for one hour, then cooled to room temperature and partitioned between 2N hydrochloric acid and diethylether. The ether extracts were purified by column chromatography (EtOAc in hexanes) to afford 584 mg of an oil (52%). 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. customThe ether extracts were purified by column chromatography (EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-db53081060104cfc8016276d64e58eb4
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723368B2

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