5-Ethyl-4-phenyl-thiophene-2-carboxylic acid → 1-(5-Ethyl-4-phenyl-thiophen-2-yl)-ethanone

HRID 552277

Reaction equation

HRID 552277 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([C:8]([OH:10])=O)=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2].[Li][CH3:18]>C1COCC1>[CH2:1]([C:3]1[S:7][C:6]([C:8](=[O:10])[CH3:18])=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2]

Participants

4

Reactant 2

HCID 671664215-Ethyl-4-phenyl-thiophene-2-carboxylic acidHCID 178418348HCID 178418348, compound2×

Product 1

HCID 671661641-(5-Ethyl-4-phenyl-thiophen-2-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 5° C. a solution of 5-ethyl-4-phenyl-thiophene-2-carboxylic acid (180 mg, 0.775 mmol) in THF (4 mL) is treated with MeLi (0.9 mL, 1.6 M in diethyl ether). The reaction mixture is stirred at rt for 30 min before another portion of MeLi (0.5 mL) is added. Stirring is continued for 1 h, the reaction is quenched by adding water (50 mL) and extracted with EA. The organic extract is dried over MgSO4, the solvent is removed in vacuo, and the crude product is purified by CC on silica gel eluting with heptane:EA 30:1 to give 1-(5-ethyl-4-phenyl-thiophen-2-yl)-ethanone (64 mg) as a colourless oil; LC-MS: tR=1.03 min, [M+1+MeCN]+=272.15; 1H NMR (CDCl3): δ 7.60 (s, 1H), 7.47-7.32 (m, 5H), 2.91 (q, J=7.6 Hz, 2H), 2.54 (s, 3H), 1.30 (t, J=7.6 Hz, 3H).

Workup

  1. additionis added
  2. customthe reaction is quenched
  3. additionby adding water (50 mL)
  4. extractionextracted with EA
  5. extractionThe organic extract
  6. dry with materialis dried over MgSO4
  7. customthe solvent is removed in vacuo
  8. customthe crude product is purified by CC on silica gel eluting with heptane:EA 30:1

Sources & evidence

ORD record
ord-105c59f248dc4ed9bae4ef820754fe68
Source dataset
uspto-grants-2011_05
Patent number
US07951794B2

Linked notes

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