Toluene → (S)-1-(3-bromo-2-methyloxyphenyl)heptane-1-ol

HRID 41529

Reaktionsgleichung

Reaktionsgleichung von HRID 41529
B.C1COCC1.C1(C)C=CC=CC=1.[Br:14][C:15]1[C:16]([O:29][CH3:30])=[C:17]([C:21](=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:18]=[CH:19][CH:20]=1>CO>[Br:14][C:15]1[C:16]([O:29][CH3:30])=[C:17]([C@@H:21]([OH:28])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:18]=[CH:19][CH:20]=1

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 2723981Borane;tetrahydrofuranHCID 595448921-(3-Bromo-2-methyloxyphenyl)heptane-1-one

Produkt 1

HCID 59544894(S)-1-(3-bromo-2-methyloxyphenyl)heptane-1-olAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Under room temperature, a 1M borane THF solution (48 mL) was added to an R-CBS 1M toluene solution (120 mL). 1-(3-Bromo-2-methyloxyphenyl)heptane-1-one (7, 13 g) was added, and the mixture was stirred for 1 hour. Methanol was added, a solvent was distilled off, and the residue was purified by chromatography to obtain (S)-1-(3-bromo-2-methyloxyphenyl)heptane-1-ol (8, 12.86 g, yield 75%).

Aufarbeitung

  1. distillationa solvent was distilled off
  2. customthe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-22e2e8a8c04640c3b9b9ef71e66d333a
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530668B2

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