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Ammonium Chloride → 1-({[tert-Butyl(diphenyl)silyl]oxy}methyl)cyclopropan-1-ol

HRID 2239228
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2239228
[Si:1]([O:18][CH2:19][C:20]([O:22]CC)=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([Mg]Br)[CH3:26].[Cl-].[NH4+]>O1CCCC1.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[Si:1]([O:18][CH2:19][C:20]1([OH:22])[CH2:26][CH2:25]1)([C:14]([CH3:15])([CH3:17])[CH3:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 59464758(tert-Butyl-diphenyl-silanyloxy)-acetic acid ethyl esterHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 529878051-({[tert-Butyl(diphenyl)silyl]oxy}methyl)cyclopropan-1-olAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11026
Titanium isopropoxide
Katalysator
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

According to the description in a reference (see: Syn. Lett. 07, 1053-1054, 1999), the title compound was prepared as follows. 12 g (35 mmole) of ethyl 2-{[t-butyl(diphenyl)silyl]oxy}acetate was dissolved in 200 ml of tetrahydrofuran (THF) and 2.2 ml of titaniumtetraisopropoxide was added thereto. To the mixture was slowly added 29.2 ml of ethylmagnesiumbromide (3.0M in THF), and the reaction solution was stirred for 12 hours at room temperature. 20 ml of saturated ammonium chloride was added to stop the reaction. About 150 ml of tetrahydrofuran (THF) used as a solvent was removed by distillation under reduced pressure, and the reaction mixture was extracted twice with 200 ml of ethyl acetate. The ethyl acetate extract was distilled under reduced pressure to give 11.4 g (Yield 100%) of the title compound as a white solid.

Aufarbeitung

  1. customthe title compound was prepared
  2. customthe reaction
  3. customwas removed by distillation under reduced pressure
  4. extractionthe reaction mixture was extracted twice with 200 ml of ethyl acetate
  5. extractionThe ethyl acetate extract
  6. distillationwas distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e0b113db60e3442391498cbcdde6319b
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07723319B2

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