Formic Acid → 3-Ethyl-5-formyl-thiophene-2-carboxylic acid methyl ester

HRID 1952626Notes

Reaction equation

HRID 1952626 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:12](OCC)[O:13]CC)=[CH:8][C:9]=1[CH2:10][CH3:11])=[O:4].C(O)=O>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:12]=[O:13])=[CH:8][C:9]=1[CH2:10][CH3:11])=[O:4]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 682273755-Diethoxymethyl-3-ethyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 866712653-Ethyl-5-formyl-thiophene-2-carboxylic acid methyl esterYield 95.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-Diethoxymethyl-3-ethyl-thiophene-2-carboxylic acid methyl ester (1.76 g, 6.46 mmol) in dioxane (16 ml) was cooled to 0° C. (ice bath). 88% formic acid (20 ml) was added in one portion and the mixture was stirred at 0° C. for 5 min and then at rt for 90 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 (1.22 g, 95% yield).

Workup

  1. waitat rt for 90 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-747e6a75b93a4097a6cfd2baf9e39c25
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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