Water → 2-(4-Phenylthiophen-2-yl)acetonitrile

HRID 1397216Notes

Reaction equation

HRID 1397216 reaction equation
O[N:2]=[C:3]([CH2:7][C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=1)C(O)=O.O>C(OC(=O)C)(=O)C>[C:13]1([C:11]2[CH:12]=[C:8]([CH2:7][C:3]#[N:2])[S:9][CH:10]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 962WaterHCID 866775892-(Hydroxyimino)-3-(4-phenylthiophen-2-yl)propanoic acid

Product 1

HCID 199347102-(4-Phenylthiophen-2-yl)acetonitrileYield 73%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

2-(Hydroxyimino)-3-(4-phenylthiophen-2-yl)propanoic acid (0.8 g, 3.1 mmol) was heated in acetic anhydride (5 mL) for 1.5 h. The reaction mixture was cooled to room temperature and treated with water. The product was extracted with EtOAc and the organic layer was washed with H2O and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 60-120 mesh, eluent 10-15% EtOAc in petroleum ether) to afford 2-(4-phenylthiophen-2-yl)acetonitrile (0.45 g, yield 73%) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.57-7.53 (m, 2H), 7.43-7.39 (m, 2H), 7.37-7.36 (m, 2H), 7.34-7.30 (m, 1H), 3.96 (s, 2H).

Workup

  1. extractionThe product was extracted with EtOAc
  2. washthe organic layer was washed with H2O and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel 60-120 mesh, eluent 10-15% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-8dc6951f2e7541e8ac14037589c4f174
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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