Reaktion #746110

ord-936982ba286b4c32838838679d158317

Reaktionsgleichung

C[Si](C)(C)[N-][Si](C)(C)C.[Li+]
Lithium bis(trimethylsilyl)amide
CCCC(Oc1ccc(Cl)cc1C1OCCO1)C(=O)OCC
2-(4-Chloro-2-[1,3]dioxolan-2-yl-phenoxy)-pentanoic acid ethyl ester
CCCI
1-Iodopropane
CCCC(CCC)(Oc1ccc(Cl)cc1C1OCCO1)C(=O)OCC
title compound
Ausbeute 67.4%
CCCC(CCC)(Oc1ccc(Cl)cc1C1OCCO1)C(=O)OCC
2-(4-chloro-2-[1,3]dioxolan-2-yl-phenoxy)-2-propyl-pentanoic acid ethyl ester
Ausbeute 67.4%

Lösungsmittel

Reaktionsbedingungen

Temperatur
-78°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturto warm to room temperature
  2. 2
    workup.STIRRINGstirred for 2 h
  3. 3
    Waschenwashed with a saturated aqueous solution of NH4Cl
  4. 4
    Trocknendried over anhydrous Na2SO4
  5. 5
    Einengenconcentrated

Vorschrift

Lithium bis(trimethylsilyl)amide (26 mL, 26 mmol, 1 M in THF) was slowly added to a solution of 2-(4-Chloro-2-[1,3]dioxolan-2-yl-phenoxy)-pentanoic acid ethyl ester (6.6 g, 20 mmol) in 60 mL of anhydrous THF at −78° C. After the mixture was stirred for 30 min at −78° C., 1-Iodopropane (4 mL, 40 mmol) was added. The mixture was allowed to warm to room temperature and stirred for 2 h. Then the mixture was diluted with ethyl acetate, washed with a saturated aqueous solution of NH4Cl, dried over anhydrous Na2SO4 and concentrated to give the title compound as a yellow oil (5 g).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08076482B2uspto-grants-2011_12