Water → HCID 12090419, compound

HRID 479286Notes

Reaction equation

HRID 479286 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]([F:10])([F:9])[F:8])[S:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].CI.[C:17]([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[CH3:17][O:1][C:2]1[CH:6]=[C:5]([C:7]([F:10])([F:8])[F:9])[S:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2759855Methyl 3-hydroxy-5-(trifluoromethyl)thiophene-2-carboxylate

Product 1

HCID 12090419HCID 12090419, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 20 g (88 mmole) of methyl 3-hydroxy-5-trifluoromethyl-2-thiophenecarboxylate in 200 mL of DMSO was added 37 g (260 mmole) of methyl iodide and 25 g (181 mmole) of powdered K2CO3. After 2 hr of stirring, the reaction mixture was poured into water and extracted with ether. The organic phase was separated, washed with water several times, dried over MgSO4, filtered and concentrated to give 20 g of a nearly colorless solid. This solid was further purified by recrystallization from 12:1 hexane:ethyl acetate to give 10.5 g of colorless crystals. The mother liquor was concentrated and purified by column chromatography to give another 8 g (87% yield). mp 78-79° C. 1H NMR (300 MHz, CDCl3): δ 7.2 (s, 1H); 4.0 (s, 3H); 3.9 (s, 3H). Anal. Calc'd for C8H7F3O3S: C, 40.00; H, 2.94; S, 13.35. Found: C, 39.87; H, 2.94; S, 13.47.

Workup

  1. extractionextracted with ether
  2. customThe organic phase was separated
  3. washwashed with water several times
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give 20 g of a nearly colorless solid
  8. customThis solid was further purified by recrystallization from 12:1 hexane

Sources & evidence

ORD record
ord-838c268cccf947e996f8878efe58f48b
Source dataset
uspto-grants-2003_11
Patent number
US06645918B1

Reaction notes

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