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

HRID 1180765ノート

反応式

HRID 1180765 の反応式
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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fc6f8a967a254e3f80f6f0a70fc24c90
出典データセット
uspto-grants-2007_10
特許番号
US07282512B2

反応ノート

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