5-(2-Methylpropyl)thiophene-2-carboxylic acid → 1-[5-(2-Methylpropyl)thiophen-2-yl]ethan-1-one

HRID 1094292Notes

Reaction equation

HRID 1094292 reaction equation
[CH2:1]([C:5]1[S:9][C:8]([C:10]([OH:12])=O)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[CH3:13][Li]>C(OCC)C>[CH2:1]([C:5]1[S:9][C:8]([C:10](=[O:12])[CH3:13])=[CH:7][CH:6]=1)[CH:2]([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 196226895-(2-Methylpropyl)thiophene-2-carboxylic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 592020141-[5-(2-Methylpropyl)thiophen-2-yl]ethan-1-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-isobutyl-thiophene-2-carboxylic acid (550 mg, 2.99 mmol) in diethyl ether (20 mL), a solution of methyl lithium (3.75 mL, 1.6 M in diethyl ether) is slowly added at rt. The reaction mixture is stirred at rt for 1 h before it is carefully washed twice with water, dried over MgSO4, filtered and evaporated to give the title compound (336 mg) as a slightly yellow oil, LC-MS: tR=0.91 min, [M+1]+=183.07.

Workup

  1. washis carefully washed twice with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-9c5bd0bff067425388c3cf79153530a4
Source dataset
uspto-grants-2012_03
Patent number
US08133910B2

Reaction notes

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