Sodium Cyanide → 4-(2-Cyanoethyl)-2,3-dihydro-benzofuran

HRID 1602406Notes

Reaction equation

HRID 1602406 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][CH2:11]OS(C)(=O)=O)[C:4]=2[CH2:3][CH2:2]1.[C-:17]#[N:18].[Na+]>CS(C)=O.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][CH2:11][C:17]#[N:18])[C:4]=2[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 54501623Methanesulfonic acid 2-(2,3-dihydrobenzofuran-4-yl)-ethyl ester

Product 1

HCID 196116994-(2-Cyanoethyl)-2,3-dihydro-benzofuranYield 99.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of methanesulfonic acid 2-(2,3-dihydrobenzofuran-4-yl)-ethyl ester (1.71 g) in dimethylsulfoxide (14 ml) was treated with sodium cyanide (381 mg) and heated at 80° for 1 h. The suspension was cooled to 20°, diluted with water (14 ml) and extracted with ethyl acetate (2×17 ml). The combined extracts were washed with 5% aqueous sodium chloride (17 ml), dried (Na2SO4) and the solvent evaporated to give the title compound (1.22 g) as a brown oil which crystallised on standing.

Workup

  1. temperatureheated at 80° for 1 h
  2. temperatureThe suspension was cooled to 20°
  3. extractionextracted with ethyl acetate (2×17 ml)
  4. washThe combined extracts were washed with 5% aqueous sodium chloride (17 ml)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-686ec95f76354d50ba0b25e48b288069
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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