Sodium Chloride → 5-(Methoxycarbonyl)-4-(trifluoromethyl)thiophene-2-carboxylic acid

HRID 1952576Notes

Reaction equation

HRID 1952576 reaction equation
[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:13])([F:12])[F:11])=[O:4].CC(=CC)C.[Cl-].[Na+].[O:23]1CCOCC1>O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:14]([OH:23])=[O:15])=[CH:8][C:9]=1[C:10]([F:11])([F:12])[F:13])=[O:4]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 105532-Methyl-2-buteneHCID 312751,4-DioxaneHCID 71742491Methyl 5-formyl-3-(trifluoromethyl)-2-thiophenecarboxylate

Product 1

HCID 682266025-(Methoxycarbonyl)-4-(trifluoromethyl)thiophene-2-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5-Formyl-3-trifluoromethyl-thiophene-2-carboxylic acid methyl ester (2.05 g, 8.61 mmol) in dioxane (40 ml) was added 2-methyl-2-butene (9 ml) and a solution of Na2ClO2 (2.34 g, 25.92 mmol) and NaH2PO4 (2.82 g) in water (9 ml). The mixture was stirred at rt for 1.5 h. The solution was saturated with sodium chloride, then successively extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to afford the desired product (2.61 g, 100% yield).

Workup

  1. extractionsuccessively extracted with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f62d040622314b56a8afd72512183921
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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