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Ammonium Chloride → 1-[1-({[Tert-butyl(dimethyl)silyl]oxy}methyl)cyclobutyl]ethanol

HRID 2062676
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2062676
[CH3:1][Mg]Br.[Si:4]([O:11][CH2:12][C:13]1([CH:17]=[O:18])[CH2:16][CH2:15][CH2:14]1)([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5].[Cl-].[NH4+]>O1CCCC1>[Si:4]([O:11][CH2:12][C:13]1([CH:17]([OH:18])[CH3:1])[CH2:14][CH2:15][CH2:16]1)([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 222444231-{[(Tert-butyldimethylsilyl)oxy]methyl}cyclobutane-1-carbaldehydeHCID 178418573HCID 178418573, Verbindung2×

Produkt 1

HCID 670086071-[1-({[Tert-butyl(dimethyl)silyl]oxy}methyl)cyclobutyl]ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Methylmagnesium bromide (21 mL, 1.0 M tetrahydrofuran solution) was cooled to 0° C., a solution of 1-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclobutanecarbaldehyde (4.0 g) in tetrahydrofuran (40 mL) was added dropwise, and the mixture was stirred at 0° C. for 1 hr. Methylmagnesium bromide (10 mL, 1.0 M tetrahydrofuran solution) was added, and the mixture was stirred at 0° C. for 30 min. The reaction mixture was added to saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as an oily compound (2.5 g, 58%).

Aufarbeitung

  1. stirringthe mixture was stirred at 0° C. for 30 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c61164330d604eb9a324fbef64d894e2
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08283353B2

Notizen zur Reaktion

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