Methyl 5-(cyanomethyl)thiophene-3-carboxylate → HCID 59698789, compound

HRID 900994Notes

Reaction equation

HRID 900994 reaction equation
C[O:2][C:3]([C:5]1[CH:9]=[C:8]([CH2:10][C:11]#[N:12])[S:7][CH:6]=1)=[O:4]>O.C(O)C>[C:11]([CH2:10][C:8]1[S:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:9]=1)#[N:12]

Participants

4

Reactant 1

HCID 57750761Methyl 5-(cyanomethyl)thiophene-3-carboxylate

Product 1

HCID 59698789HCID 59698789, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 5-cyanomethyl-thiophene-3-carboxylic acid methyl ester (4.4 g, 22.1 mmol) and NHCO3 (4.1 g, 48.6 mmol) in water (35 mL) and ethanol (35 mL) is heated to reflux for 4 h. After cooling, the reaction mixture is diluted with water and washed with ether. The aqueous layer is acidified with 1 N HCl and extracted with dichloromethane (4×). The combined organic layers are washed with saturated aq NaCl, dried over Na2SO4, filtered and concentrated in vacuo to give 5-cyanomethyl-thiophene-3-carboxylic acid (2.7 g, 73%) as a light yellow solid: mp 154-159° C.; 1H NMR (DMSO-d6, 300 MHz) δ 12.72 (s, 1 H), 8.20 (s, 1 H), 7.30 (s, 1 H), 4.23 (s, 2 H).

Workup

  1. temperatureto reflux for 4 h
  2. temperatureAfter cooling
  3. washwashed with ether
  4. extractionextracted with dichloromethane (4×)
  5. washThe combined organic layers are washed with saturated aq NaCl
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-62378ab52de34f8a856c3301fc2ebcd4
Source dataset
uspto-grants-2008_04
Patent number
US07361671B2

Reaction notes

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