Ethyl Acetate → HCID 15296961, compound

HRID 374517Notes

Reaction equation

HRID 374517 reaction equation
[Cl:1][O-].[Na+].[S:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]1[NH:10][C:11]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:13]=1[C:14]#[N:15].C(OCC)(=O)C>O1CCCC1.CCCCCC>[Cl:1][C:12]1[C:13]([C:14]#[N:15])=[C:9]([C:5]2[S:4][CH:8]=[CH:7][CH:6]=2)[NH:10][C:11]=1[C:16]([F:19])([F:17])[F:18]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 15296963HCID 15296963, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 15296961HCID 15296961, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Sodium hypochlorite (12 mL of a 5.25% solution, 17 mmol) is added dropwise to a solution of 2-(2-thienyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile (2.00 g, 8.26 mmol) in tetrahydrofuran. The reaction mixture is stirred for 2 hours and 15 minutes, quenched with a 1% sodium bisulfite solution and diluted with ether. The layers are separated and the organic layer is washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo to obtain a yellow solid. Flash chromatography of the solid using silica gel and a 15% ethyl acetate in hexane solution gives a solid which is recrystallized from ethyl acetate and hexane to obtain the title product as a yellow solid (0.35 g, 15%, mp 221°-223° C.).

Workup

  1. customquenched with a 1% sodium bisulfite solution
  2. additiondiluted with ether
  3. customThe layers are separated
  4. washthe organic layer is washed sequentially with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto obtain a yellow solid
  8. customis recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-e144b9d3b54443fdbe59079d00dcb1e6
Source dataset
uspto-grants-1996_01
Patent number
US05480902

Reaction notes

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