Water → HCID 71226844, compound

HRID 869458Notes

Reaction equation

HRID 869458 reaction equation
[Cl:1][C:2]1[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([CH3:9])[S:5][C:6]=1[CH:7]=[O:8].[OH:15]OS([O-])=O.[K+].O>CN(C=O)C>[Cl:1][C:2]1[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([CH3:9])[S:5][C:6]=1[C:7]([OH:15])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 12605980HCID 12605980, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 71226844HCID 71226844, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of ethyl 4-chloro-5-formyl-2-methylthiophene-3-carboxylate (F-4) (9.72 g, 41.77 mmol, 1.0 eq) in DMF (150 mL), Oxone (77.1 g, 125.3 mmol, 3.0 eq) is added in portions and the resulting mixture is stirred at RT overnight. The mixture is poured into H2O (800 mL) and stirred for 30 min. The precipitate is collected by filtration, rinsed with H2O (100 mL) and then slurried in H2O (80 mL) for 30 min. The solid is collected by filtration, rinsed with H2O (3×60 mL) and petroether (3×60 mL), and dried in vacuo to afford the product, 3-chloro-4-(ethoxycarbonyl)-5-methylthiophene-2-carboxylic acid (F-5).

Workup

  1. additionis added in portions
  2. stirringstirred for 30 min
  3. filtrationThe precipitate is collected by filtration
  4. washrinsed with H2O (100 mL)
  5. waitslurried in H2O (80 mL) for 30 min
  6. filtrationThe solid is collected by filtration
  7. washrinsed with H2O (3×60 mL) and petroether (3×60 mL)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-32cc058b733549428b3f9efacc6ca07e
Source dataset
uspto-grants-2015_03
Patent number
US08969363B2

Reaction notes

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