Water → HCID 71226844, compound

HRID 2173467Notes

Reaction equation

HRID 2173467 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 H7O (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 H7O (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-28b45edd29514a76b809a948b15788c1
Source dataset
uspto-grants-2015_06
Patent number
US09056877B2

Reaction notes

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