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

HRID 1180765노트

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HRID 1180765 반응식
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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매2회HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

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온도
130 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fc6f8a967a254e3f80f6f0a70fc24c90
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282512B2

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