Potassium Cyanide → 2-(2,3-Dihydrobenzofuran-6-yl)acetonitrile

HRID 869869Notes

Reaction equation

HRID 869869 reaction equation
Cl[CH2:2][C:3]1[CH:11]=[CH:10][C:6]2[CH2:7][CH2:8][O:9][C:5]=2[CH:4]=1.[C-:12]#[N:13].[K+]>CS(C)=O.O>[O:9]1[C:5]2[CH:4]=[C:3]([CH2:2][C:12]#[N:13])[CH:11]=[CH:10][C:6]=2[CH2:7][CH2:8]1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 215538426-(Chloromethyl)-2,3-dihydrobenzofuran

Product 1

HCID 687251442-(2,3-Dihydrobenzofuran-6-yl)acetonitrileYield 72.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 6-(chloromethyl)-2,3-dihydrobenzofuran (12.3 g, 73 mmol) in DMSO (100 mL) was added KCN (7.1 g, 109.5 mmol). The reaction mixture was stirred at 100 □ for 2 hours. The mixture was diluted with water and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with brine, dried, concentrated in vacuo and purified by column chromatography on silica gel (5-10% ethyl acetate in petroleum ether) to afford 2-(2,3-dihydrobenzofuran-6-yl)acetonitrile (8.4 g, 70.4% yield). 1H NMR (400 MHz, CDCl3) δ: 7.16 (d, J=7.6, 1H), 6.79 (d, J=7.2, 1H), 6.72 (s, 1H), 4.58 (t, J=8.4, 2H), 3.67 (s, 2H), 3.19 (t, J=8.4, 2H).

Workup

  1. extractionextracted with ethyl acetate (3×200 mL)
  2. washThe combined organic layers were washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography on silica gel (5-10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-c5375771f25f47aeb3f978639a5fdf66
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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