Potassium Cyanide → HCID 68943961, compound

HRID 900985Notes

Reaction equation

HRID 900985 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([CH3:13])=[C:9]([CH2:11]Cl)[CH:10]=1)=[O:5])[CH3:2].[C-:14]#[N:15].[K+]>CN(C=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([CH3:13])=[C:9]([CH2:11][C:14]#[N:15])[CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 57750758HCID 57750758, compound

Product 1

HCID 68943961HCID 68943961, compoundYield 18.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of the 4-chloromethyl-5-methyl-thiophene-2-carboxylic acid ethyl ester mixture from part 2 (25.6 g) in DMF (350 mL) is treated with potassium cyanide (20 g, 0.312 mol) and heated to 70° C. with stirring for 2 h. After cooling to room temperature, the solution is diluted with water and extracted with chloroform (2×). The combined organic layers are washed with saturated aq NaCl, dried over Na2SO4, filtered and concentrated in vacuo. The residue is purified by flash chromatography (10% ethyl acetate in heptane) to give 4-cyanomethyl-5-methyl-thiophene-2-carboxylic acid ethyl ester (4.7 g, 18.8%; 2 steps) as a white solid. mp 55-57° C.; 1H NMR (CDCl3, 300 MHz) δ 7.63 (s, 1 H), 4.28 (q, J=6.0 Hz, 2 H), 3.60 (s, 2 H), 2.48 (s, 3 H), 1.38 (t, J=6.0 Hz, 3 H).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with chloroform (2×)
  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 flash chromatography (10% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-69a4590c89f545e28d6a435648011471
Source dataset
uspto-grants-2008_04
Patent number
US07361671B2

Reaction notes

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