Potassium Cyanide → HCID 68940385, compound

HRID 900997Notes

Reaction equation

HRID 900997 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10]Cl)[CH:9]=1.[C-:13]#[N:14].[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][C:13]#[N:14])[CH:9]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 57750763HCID 57750763, compound

Product 1

HCID 68940385HCID 68940385, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (4-chloromethyl-thiophen-2-yl)-acetic acid methyl ester (0.58 g, 2.83 mmol) and potassium cyanide (0.39 g, 5.95 mmol) in DMF (15 mL) is stirred at room temperature for 14 h then heated to 50° C. for 0.5 h. The mixture is quenched with saturated aq NaCl and extracted with CHCl3 (3×). The combined organic layers are washed with saturated aq NaCl, dried over Na2SO4, filtered and concentrated in vacuo. The residue is purified by chromatography (silica gel, 10% ethyl acetate in heptane) to give (4-cyanomethyl-thiophen-2-yl)-acetic acid methyl ester (0.43 g, 78%) as a colorless oil: 1H NMR (CDCl3, 300 MHz) δ 7.10 (s, 1 H), 6.95 (s, 1 H), 3.80 (s, 2 H), 3.72 (s, 3 H), 3.65 (s, 2 H).

Workup

  1. customThe mixture is quenched with saturated aq NaCl
  2. extractionextracted with CHCl3 (3×)
  3. washThe combined organic layers are washed with saturated aq NaCl
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by chromatography (silica gel, 10% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-eb1a041182f14a7dbcd58443e4e4ae5f
Source dataset
uspto-grants-2008_04
Patent number
US07361671B2

Reaction notes

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