Dimethyl Sulfoxide → Methyl 5-formyl-3-phenylthiophene-2-carboxylate

HRID 1186715Notes

Reaction equation

HRID 1186715 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][C:13]1[S:17][C:16]([C:18]([O:20][CH3:21])=[O:19])=[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:14]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:12]([C:13]1[S:17][C:16]([C:18]([O:20][CH3:21])=[O:19])=[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:14]=1)=[O:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 58121059Methyl 5-(hydroxymethyl)-3-phenylthiophene-2-carboxylate

Product 1

HCID 71742493Methyl 5-formyl-3-phenylthiophene-2-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
0 °C

Procedure

DMSO (0.643 ml, 9.06 mmol) in 4 mL of DCM at −70° C. was added dropwise to a solution of oxalyl chloride (0.529 ml, 6.04 mmol) in 10 mL of DCM at −78° C. and stirred for 10 min. Then 169 (0.75 g, 3.02 mmol) in 4 mL of DCM and TEA in 4 ml, DCM were added dropwise, stirred for an additional 10 min and warmed up slowly to 0° C. The reaction mixture was poured into an ice-cooled solution of NaHCO3 (ss) and extract the product with DCM, washed with brine, dried over sodium sulfate, filtered, concentrated under vacuum to yield compound 172 (706 mg, 95%) as a beige solid.

Workup

  1. stirringstirred for an additional 10 min
  2. extractionextract the product with DCM
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ff0731efb20348b9810dcea1f07410ff
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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