Chloroform → 1-{4-Hydroxy-5-[4-(trifluoromethoxy)phenyl]thiophen-3-yl}ethan-1-one

HRID 239222Notes

Reaction equation

HRID 239222 reaction equation
C(Cl)(Cl)Cl.[F:5][C:6]([F:24])([F:23])[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[C:18]([OH:19])=[C:17]([C:20]([CH3:22])=[O:21])[CH2:16][S:15]2)=[CH:10][CH:9]=1.S(Cl)(Cl)(=O)=O>O>[F:24][C:6]([F:5])([F:23])[O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[S:15][CH:16]=[C:17]([C:20]([CH3:22])=[O:21])[C:18]=2[OH:19])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6212Chloroform2×HCID 24648Sulfuryl chlorideHCID 44207283HCID 44207283, compound

Product 1

HCID 442075211-{4-Hydroxy-5-[4-(trifluoromethoxy)phenyl]thiophen-3-yl}ethan-1-oneYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-15 °C

Procedure

A chloroform (45 mL) solution of 2-(4-trifluoromethoxyphenyl)-3-hydroxy-4-methylcarbonyl-2,5-dihydrothiophene (4.5 g, 12.6 mmol, purity: 85%) was cooled to −5° C., and to this solution, a chloroform (90 mL) solution of sulfuryl chloride (1.1 mL, 1.1 equivalent amounts) was dropwise added over a period of 30 minutes, followed by stirring at −15° C. for 1 hour. The temperature of the solution was raised to 0° C., and water (11 mL) was dropwise added, followed by liquid separation. The obtained chloroform solution was sequentially washed with water, a saturated salt solution, a sodium hydroxide aqueous solution, a saturated sodium thiosulfate aqueous solution and a saturated salt solution, and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was distilled off to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to give the desired product as a yellow solid (3.15 g, yield: 83%).

Workup

  1. temperatureThe temperature of the solution was raised to 0° C.
  2. customfollowed by liquid separation
  3. washThe obtained chloroform solution was sequentially washed with water
  4. dry with materiala saturated salt solution, a sodium hydroxide aqueous solution, a saturated sodium thiosulfate aqueous solution and a saturated salt solution, and dried over anhydrous magnesium sulfate
  5. customThe drying agent was removed by filtration
  6. distillationthe solvent was distilled off
  7. customto obtain a crude product
  8. customThe obtained crude product
  9. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9cdefc1547d445ad9955b4face4f1adf
Source dataset
uspto-grants-2014_02
Patent number
US08642786B2

Reaction notes

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