Water → 1-Allyl-3-methylcyclobutanol

HRID 20050Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 20050
C[CH:2]1[CH2:5][CH2:4][C:3]1=[O:6].[CH2:7]([Mg]Br)[CH:8]=[CH2:9].O.[CH2:13]1COCC1>>[CH2:7]([C:3]1([OH:6])[CH2:2][CH:5]([CH3:13])[CH2:4]1)[CH:8]=[CH2:9]

Komponenten

5

Edukt 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 151992-Methylcyclobutan-1-oneHCID 178455850HCID 178455850, Verbindung

Produkt 1

HCID 673052351-Allyl-3-methylcyclobutanolAusbeute 46,9 %

Versuchsvorschrift

Methylcyclobutanone (3.200 g, 38.043 mmol) was dissolved in 200 ml THF and allylmagnesium bromide (190.21 ml, 190.21 mmol) was added in one portion. The mixture was stirred for 4 h at RT, hydrolyzed with water and extracted. The combined organic extracts were dried over MgSO4 and evaporated and purified via glass col. Chrom. (25-75% hex. in EtOAc). 1-Allyl-3-methylcyclobutanol (2.250 g, 46.9% yield) was obtained as a mixture of cis-trans isomers approx 4:1 (where the major compound is the one Me-cis to OH) based on NMR.

Aufarbeitung

  1. extractionextracted
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. customevaporated
  4. custompurified via glass col

Quellen und Nachweise

ORD-Eintrag
ord-5a21bab2a39b4e56a4ba1ff98b5872cb
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745484B2

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