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

HRID 1180765Notes

Reaction equation

HRID 1180765 reaction equation
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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-fc6f8a967a254e3f80f6f0a70fc24c90
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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