Sulfuric Acid → Methyl 3-hydroxy-5-(trifluoromethyl)thiophene-2-carboxylate

HRID 362177Notes

Reaction equation

HRID 362177 reaction equation
[OH-].[K+].CO[C:5]([C:12]([F:15])([F:14])[F:13])=[CH:6][C:7]([O:9]CC)=O.[C:16]([O:20][CH3:21])(=[O:19])[CH2:17][SH:18].S(=O)(=O)(O)O>CO>[OH:9][C:7]1[CH:6]=[C:5]([C:12]([F:13])([F:14])[F:15])[S:18][C:17]=1[C:16]([O:20][CH3:21])=[O:19]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 16907Methyl ThioglycolateHCID 27588673-Methoxy-4,4,4-trifluoro-2-butenoic acid ethyl ester

Product 1

HCID 2759855Methyl 3-hydroxy-5-(trifluoromethyl)thiophene-2-carboxylateYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 1M potassium hydroxide in methanol (30 ml) is added to a cooled mixture of 1A (4.6 g), methyl thioglycolate (2.46 g) and methanol (10 ml). The resulting reaction mixture was stirred for 24 hours at room temperature. Then the mixture was poured on ice and acidified with 6N sulfuric acid (pH=2). The mixture is extracted with diethyl ether twice. The combined organic phases were washed with water and dried. The mixture was concentrated and the residue is distilled under reduced pressure to yield the product as a clear liquid (3.4 g, 65%) with a boiling point of 42°-45° C. at 0.10 mm.

Workup

  1. customThe resulting reaction mixture
  2. additionThen the mixture was poured on ice
  3. extractionThe mixture is extracted with diethyl ether twice
  4. washThe combined organic phases were washed with water
  5. customdried
  6. concentrationThe mixture was concentrated
  7. distillationthe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-9551cf5cc77942b6aaf589d6aac95684
Source dataset
uspto-grants-1999_02
Patent number
US05869426

Reaction notes

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