Diethyl Ether → Methyl 5-acetylthiophene-2-carboxylate

HRID 588494Notes

Reaction equation

HRID 588494 reaction equation
[C:1]([C:4]1[S:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:12][Si](C=[N+]=[N-])(C)C.CCOCC>C1(C)C=CC=CC=1.CO>[C:1]([C:4]1[S:8][C:7]([C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 37427275-Acetylthiophene-2-carboxylic acid

Product 1

HCID 13156400Methyl 5-acetylthiophene-2-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-acetylthiophene-2-carboxylic acid (3.24 g, 19.0 mmol) dissolved in a mixture of toluene (50 mL) and methanol (50 mL) cooled to 0° C. was added 2.0 M trimethylsilyldiazomethane in ether (19.0 mL, 38.1 mmol) dropwise. Upon complete addition, the reaction mixture was allowed to warm to room temperature overnight. The reaction was quenched with the addition of acetic acid and the solvent was removed. The residue thus obtained was partitioned between ethyl acetate and saturated aqueous NaHCO3 and upon separation, the organic layer was dried over anhydrous magnesium sulfate and concentrated to afford the desired product (3.49 g, 100%). LC-MS: (FA) ES+ 185)

Workup

  1. additionUpon complete addition
  2. temperatureto warm to room temperature overnight
  3. customThe reaction was quenched with the addition of acetic acid
  4. customthe solvent was removed
  5. customThe residue thus obtained
  6. customwas partitioned between ethyl acetate and saturated aqueous NaHCO3 and upon separation
  7. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b95d1ce47ce84b59a2d0180049d86d2b
Source dataset
uspto-grants-2016_01
Patent number
US09227951B2

Reaction notes

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