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

HRID 1952563Notes

Reaction equation

HRID 1952563 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:11]=[O:12])=[CH:8][C:9]=1[CH3:10])=[O:4].CC(=CC)C.[Cl-].[Na+].[O:20]1CCOCC1>O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]([OH:20])=[O:12])=[CH:8][C:9]=1[CH3:10])=[O:4]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 105532-Methyl-2-buteneHCID 312751,4-DioxaneHCID 57618829Methyl 5-formyl-3-methylthiophene-2-carboxylate

Product 1

HCID 682266195-(Methoxycarbonyl)-4-methylthiophene-2-carboxylic acidYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5-formyl-3-methyl-thiophene-2-carboxylic acid methyl ester (3.2 g, 17.4 mmol) in dioxane (20 ml) was added 2-methyl-2-butene (15 ml) and a solution of Na2ClO2 (4.71 g, 52.1 mmol) and NaH2PO4 (4.71 g, 39.2 mmol) in water (15 ml). The mixture was stirred at rt for 1 h. The solution was saturated with sodium chloride, then successively extracted with EtOAc and dichloromethane. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to afford the desired product (3.13 g, 90% yield)

Workup

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

Sources & evidence

ORD record
ord-b8f669c751c148ecba9fdd0b9e2907e8
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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