Sodium Chloride → HCID 57750759, compound

HRID 900988Notes

Reaction equation

HRID 900988 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:9]=[C:8]([CH2:10]Cl)[S:7][C:6]=1[CH3:12].[C-:14]#[N:15].[K+].C(Cl)(Cl)Cl.[Na+].[Cl-]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:9]=[C:8]([CH2:10][C:14]#[N:15])[S:7][C:6]=1[CH3:12]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6212ChloroformHCID 9032Potassium CyanideHCID 57750760HCID 57750760, compound

Product 1

HCID 57750759HCID 57750759, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (5-chloromethyl-2-methyl-thiophen-3-yl)-acetic acid methyl ester (2.6 g, 12.1 mmol) and potassium cyanide (1.7 g, 25.4 mmol) in DMF (33 mL) is stirred for 14 h at room temperature then warmed to 50° C. for 0.5 h. After cooling, the mixture is poured into a mixture of CHCl3 and saturated aq NaCl and extracted with CHCl3. The combined extracts are washed with saturated aq NaCl, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue is purified by flash chromatography (silica gel, 10-50% ethyl acetate in heptane) to give (5-cyanomethyl-2-methyl-thiophen-3-yl)-acetic acid methyl ester (1.1 g, 43.4%): 1H NMR (CDCl3, 300 MHz) δ 6.83 (s, 1 H), 3.80 (s, 2 H), 3.70 (s, 3 H), 3.50 (s, 2 H), 2.38 (s, 3 H).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with CHCl3
  3. washThe combined extracts are washed with saturated aq NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue is purified by flash chromatography (silica gel, 10-50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-7f0ffa2375d141c4985e0487ece538cf
Source dataset
uspto-grants-2008_04
Patent number
US07361671B2

Reaction notes

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