Water → (3-Bromo-5-{[tert-butyl(dimethyl)silyl]oxy}phenyl)methanol

HRID 1513101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1513101
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH:9]=1)[CH:5]=[O:6].[BH4-].[Na+].O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[C:8]([O:10][Si:11]([C:14]([CH3:15])([CH3:16])[CH3:17])([CH3:13])[CH3:12])[CH:9]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 577919013-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-benzaldehyde

Produkt 1

HCID 57791917(3-Bromo-5-{[tert-butyl(dimethyl)silyl]oxy}phenyl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-benzaldehyde (7 g, 22.2 mmol) was dissolved in THF and sodium borohydride (0.92 g; 24.4 mmol) was added. The reaction mixture was stirred at room temperature for 2 h and water was added, and the reaction mixture was partly evaporated to strip off THF. Ethyl acetate was added and the phases separated. The organic phase was washed with water, dried, and evaporated to dryness. Yield: 6.4 g; HPLC-MS: m/z: 317.0 (M+); Rt: 2.37 min.

Aufarbeitung

  1. customthe reaction mixture was partly evaporated
  2. additionEthyl acetate was added
  3. customthe phases separated
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-783e7be33ec24d9ba269d537acf4c51f
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217086B2

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