Water → 1-Allyl-3-methylcyclobutanol

HRID 1009156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009156
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-e75f53b11d424d529f717d61d44aee73
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973047B2

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