Formic Acid → Methyl 5-formyl-3-phenylthiophene-2-carboxylate

HRID 1952588Notes

Reaction equation

HRID 1952588 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:16](OCC)[O:17]CC)=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:4].C(O)=O>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:16]=[O:17])=[CH:8][C:9]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:4]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 682267945-Diethoxymethyl-3-phenyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 71742493Methyl 5-formyl-3-phenylthiophene-2-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-Diethoxymethyl-3-phenyl-thiophene-2-carboxylic acid methyl ester (5.07 g, 15.82 mmol) in dioxane (25 ml) was cooled to 0° C. (ice bath). 95% formic acid (50 ml) was added dropwise and the mixture was stirred at 0° C. for 30 min and then at rt for 60 min. The reaction mixture was quenched by pouring into EtOAc. The organic layer was washed with water, dried over Na2SO4 and concentrated under reduced pressure to afford the desired product (3.50 g, 90% yield).

Workup

  1. waitat rt for 60 min
  2. customThe reaction mixture was quenched
  3. additionby pouring into EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-62e3d47a4e1643cda3cc6b92872f8351
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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