5-methyl-4-phenyl-2-thiophenecarboxylic acid → Ethanone, 1-(5-methyl-4-phenyl-2-thienyl)-

HRID 552271Notes

Reaction equation

HRID 552271 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Li][CH3:17]>C(OCC)C.O>[CH3:1][C:2]1[S:6][C:5]([C:7](=[O:9])[CH3:17])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 8219265-methyl-4-phenyl-2-thiophenecarboxylic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 818940Ethanone, 1-(5-methyl-4-phenyl-2-thienyl)-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-methyl-4-phenyl-thiophene-2-carboxylic acid (1.50 g, 6.87 mmol) in diethyl ether (100 mL) MeLi (7 mL, 1.5 M in diethyl ether) is added at 5° C. The mixture is stirred at it for 90 min before another portion of MeLi (1 mL) is added. Stirring is continued for 1 h. The mixture is diluted with water and extracted with EA. The organic extracts are evaporated and the crude product is purified by CC on silica gel eluting with heptane:EA 4:1 to give 1-(5-methyl-4-phenyl-thiophen-2-yl)-ethanone (490 mg) as a colourless oil, LC-MS: tR=1.00 min, [M+1]+=217.10; 1H NMR (CDCl3): δ 7.62 (s, 1H), 7.48-7.33 (m, 5H), 2.54 (s, 6H).

Workup

  1. additionis added
  2. extractionextracted with EA
  3. customThe organic extracts are evaporated
  4. customthe crude product is purified by CC on silica gel eluting with heptane:EA 4:1

Sources & evidence

ORD record
ord-0a9efe6aa51a4d48937a493c56c572f4
Source dataset
uspto-grants-2011_05
Patent number
US07951794B2

Reaction notes

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