Reaktion #1436629

ord-dd27a7b685d449708c8f368841ab3425

Reaktionsgleichung

C[C@@H]1[C@@H](B(Cl)[C@H]2C[C@H]3C[C@@H]([C@@H]2C)C3(C)C)C[C@H]2C[C@@H]1C2(C)C
(+)-B-chlorodiisopinocampheylborane
COc1ccccc1C(C)=O
2′methoxyacetophenone
COc1ccccc1[C@@H](C)O
title compound
Ausbeute 75.2%
COc1ccccc1[C@@H](C)O
(R)-1-(2-Methoxyphenyl)ethanol
Ausbeute 75.2%

Lösungsmittel

Reaktionsbedingungen

Temperatur
-25°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Einengenconcentrated under reduced pressure
  2. 2
    workup.ADDITIONTo the residue were added diethyl ether (100 ml) and diethanolamine (18.1 g)
  3. 3
    workup.STIRRINGthe reaction mixture was stirred at room temperature for 2 hr
  4. 4
    FiltrationThe precipitated solid was filtered off
  5. 5
    EinengenThe filtrate was concentrated under reduced pressure
  6. 6
    workup.DISTILLATIONpurified by distillation under reduced pressure (bp 74–77° C./1 mmHg)

Vorschrift

To a solution of (+)-B-chlorodiisopinocampheylborane (10.5 g) in tetrahydrofuran (50 ml) was added dropwise 2′methoxyacetophenone (10.5 g) at −25° C. The mixture was stirred at −25° C. for 1 hr and concentrated under reduced pressure. To the residue were added diethyl ether (100 ml) and diethanolamine (18.1 g) and the reaction mixture was stirred at room temperature for 2 hr. The precipitated solid was filtered off. The filtrate was concentrated under reduced pressure and purified by distillation under reduced pressure (bp 74–77° C./1 mmHg) to give the title compound (8.00 g).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07211685B2uspto-grants-2007_05