Formic Acid → Methyl 5-formyl-3-(trifluoromethyl)-2-thiophenecarboxylate

HRID 1952575Notes

Reaction equation

HRID 1952575 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:14](OCC)[O:15]CC)=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])=[O:4].C(O)=O>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:14]=[O:15])=[CH:8][C:9]=1[C:10]([F:11])([F:12])[F:13])=[O:4]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 682265135-Diethoxymethyl-3-trifluoromethyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 71742491Methyl 5-formyl-3-(trifluoromethyl)-2-thiophenecarboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-Diethoxymethyl-3-trifluoromethyl-thiophene-2-carboxylic acid methyl ester (2.72 g, 8.71 mmol) in dioxane (20 ml) was cooled to 0° C. (ice bath). 88% formic acid (25 ml) was added in one portion and the mixture was stirred at 0° C. for 5 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 (2.05 g, 99% yield).

Workup

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

Sources & evidence

ORD record
ord-779abd9d39f14d3d86c285b4561ec061
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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