Sodium hydride → [2-Bromo-5-(1-hydroxy-1-methyl-ethyl)-benzyl]-ethyl-carbamic acid benzyl ester

HRID 1920022

Reaktionsgleichung

Reaktionsgleichung von HRID 1920022
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:4][C:3]=1[CH2:12]Br.[CH2:14]([O:21][C:22](=[O:26])[NH:23][CH2:24][CH3:25])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[H-].[Na+]>CN(C=O)C>[CH2:14]([O:21][C:22](=[O:26])[N:23]([CH2:12][C:3]1[CH:4]=[C:5]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:6]=[CH:7][C:2]=1[Br:1])[CH2:24][CH3:25])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 12384304benzyl N-ethylcarbamateHCID 574198682-(4-Bromo-3-bromomethyl-phenyl)-propan-2-ol

Produkt 1

HCID 58149231[2-Bromo-5-(1-hydroxy-1-methyl-ethyl)-benzyl]-ethyl-carbamic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 2-(4-bromo-3-bromomethyl-phenyl)-propan-2-ol (0.255 g, 0.83 mmol) and ethyl-carbamic benzyl ester (0.446 g, 2.49 mmol) in DMF (15 mL) was added sodium hydride (60% in mineral oil; 0.103 g, 2.57 mmol), and the reaction was stirred for 30 minutes. The mixture was quenched with H2O and worked-up. The residue was purified by silica gel chromatography (0-40% EtOAc in hexanes) to give the title compound.

Aufarbeitung

  1. customThe mixture was quenched with H2O
  2. customThe residue was purified by silica gel chromatography (0-40% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3f28ecb951ed472781532c341ca50f14
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08168678B2

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