Nitrogen → 1-(3-[Tert-butyl(diphenyl)silyl]oxycyclobutyl)ethanone

HRID 1692945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1692945
[Si:1]([O:18][CH:19]1[CH2:22][CH:21]([C:23](N(OC)C)=[O:24])[CH2:20]1)([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.[CH3:29][Mg]I.N#N>CCOCC>[Si:1]([O:18][CH:19]1[CH2:20][CH:21]([C:23](=[O:24])[CH3:29])[CH2:22]1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 947NitrogenHCID 866343493-((tert-Butyldiphenylsilyl)oxy)-N-methoxy-N-methylcyclobutanecarboxamideHCID 178418373HCID 178418373, Verbindung

Produkt 1

HCID 668242881-(3-[Tert-butyl(diphenyl)silyl]oxycyclobutyl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of 3-[tert-butyl(diphenyl)silyl]oxy-N-methoxy-N-methylcyclobutanecarboxamide (0.7 g, 0.002 mol) in ether (10 mL) was added into 3.0 M of methylmagnesium iodide in ether (3 mL) slowly under N2. The reaction was stirred and heated to reflux for 2 h. The mixture was quenched with ice and the ether layer separated. The aq. layer was acidified with 1N HCl and extracted several times with ether. The organic layers were combined, dried over MgSO4, concentrated and purified with Combiflash (silica gel, 0-30% EtOAc/Hex) to give the desired product (0.6 g) as colorless oil. LCMS calculated for C22H29O2Si(M+H)+: 353.2; Found: 353.3.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. customThe mixture was quenched with ice
  4. customthe ether layer separated
  5. extractionextracted several times with ether
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. custompurified with Combiflash (silica gel, 0-30% EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-2336e435736d4b5cb51f73a04011942f
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158616B2

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