Potassium Cyanide → {1-[(Benzyloxy)methyl]cyclobutyl}acetonitrile

HRID 1180765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1180765
CS(O[CH2:6][C:7]1([CH2:11][O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9][CH2:8]1)(=O)=O.[C-:20]#[N:21].[K+]>CN(C)C=O.O.CCOCC>[CH2:13]([O:12][CH2:11][C:7]1([CH2:6][C:20]#[N:21])[CH2:10][CH2:9][CH2:8]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 2

HCID 9032Potassium CyanideHCID 11346646{1-[(Benzyloxy)methyl]cyclobutyl}methyl methanesulfonate

Produkt 1

HCID 11148614{1-[(Benzyloxy)methyl]cyclobutyl}acetonitrileAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a solution of 16.75 g (59.0 mmol) of {1-[(benzyloxy)methyl]cyclobutyl}methyl methanesulfonate in 150 mL of N,N-dimethylformamide and 15 mL of water was added 4.97 g (88.5 mmol) of potassium cyanide and the contents heated at 130° C. for 5 h. The reaction mixture was cooled, diluted with ether and water, and the layers separated. The organic phase was dried using magnesium sulfate and concentrated under vacuum to afford the crude product, which was purified by silica gel chromatography using ethyl acetate/hexane (1:3) as the eluent to afford 8.0 g (88%) of {1-[(benzyloxy)methyl]cyclobutyl}acetonitrile as a colorless oil. 1H NMR (300 MHz, CDCl3). 1H NMR (300 MHz, CDCl3) δ 7.43-7.29 (m, 5H), 4.59 (s, 2H), 3.5 (s, 2H), 2.6 (s, 2H), 2.08-1.92 (m, 6H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. customthe layers separated
  3. customThe organic phase was dried
  4. concentrationconcentrated under vacuum
  5. customto afford the crude product, which
  6. customwas purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fc6f8a967a254e3f80f6f0a70fc24c90
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07282512B2

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