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

HRID 576363

反応式

HRID 576363 の反応式
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

参加物

4

反応物 3

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

生成物 1

HCID 783192,3-Dihydrobenzo(b)thiophene収率 41%

反応条件

温度
50 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-9cf68d3f61914dd9a8bc48172da99ed6
出典データセット
uspto-grants-2015_05
特許番号
US09034921B2

関連ノート

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