Trifluoroacetic acid → 2,3-Dihydrobenzo(b)thiophene

HRID 576363

Reaction equation

HRID 576363 reaction equation
FC(F)(F)C(O)=O.[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH:10]=[CH:9]1.C([SiH](CC)CC)C>>[S:8]1[CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]1=2

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7221Benzo(B)ThiopheneHCID 12052Triethylsilane

Product 1

HCID 783192,3-Dihydrobenzo(b)thiopheneYield 41%

Conditions

Temperature
50 °C

Procedure

Trifluoroacetic acid (5.2 mL) was slowly added to the mixture of benzothiophene (1 g, 7.45 mmol) and triethylsilane (3.6 mL, 22.35 mmol) with heating under reflux at 50° C. for 125 hours. After cooling to 0° C., the reaction was quenched by addition of aq. saturated NH4Cl solution. The mixture was diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography to provide the intermediate 112 (415 mg, 41%).

Workup

  1. temperaturewith heating
  2. temperatureAfter cooling to 0° C.
  3. customthe reaction was quenched by addition of aq. saturated NH4Cl solution
  4. additionThe mixture was diluted with water
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9cf68d3f61914dd9a8bc48172da99ed6
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Linked notes

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