Sodium borohydride → 1-(4-Bromo-3-methyl-phenyl)-5-methyl-hexan-1-ol

HRID 1669329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669329
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:4][C:3]=1[CH3:16].[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:13])[CH3:14])=[CH:4][C:3]=1[CH3:16]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 673424431-(4-Bromo-3-methyl-phenyl)-5-methyl-hexan-1-one

Produkt 1

HCID 673450331-(4-Bromo-3-methyl-phenyl)-5-methyl-hexan-1-olAusbeute 94,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-(4-Bromo-3-methyl-phenyl)-5-methyl-hexan-1-one (3.5 g, 12.4 mmol) was dissolved in ethanol and cooled to 0° C. while stirring under nitrogen. To the flask was added sodium borohydride (469 mg, 12.4 mmol), and the reaction was kept at 0° C. for 1 h., then slowly warmed to room temperature. The reaction was monitored by HPLC. Upon complete consumption of starting material, the reaction is carefully quenched with water, the ethanol removed by rotary evaporator, and extracted with diethyl ether, washed, dried, and concentrated. The title compound (3.33 g, 11.72 mmol), is used in the next step without further purification.

Aufarbeitung

  1. temperatureslowly warmed to room temperature
  2. customUpon complete consumption of starting material
  3. customthe reaction is carefully quenched with water
  4. customthe ethanol removed by rotary evaporator
  5. extractionextracted with diethyl ether
  6. washwashed
  7. customdried
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-72b9b7aab46c4078a77272c2e0b35549
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989457B2

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