Trifluoroacetic acid → ethyl 6-chloro-7-(thien-2-ylmethyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854982ノート

反応式

HRID 854982 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH:12](O)[C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)[O:8][CH:7]([C:19]([F:22])([F:21])[F:20])[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:5]2.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)[O:8][CH:7]([C:19]([F:22])([F:21])[F:20])[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:5]2

参加物

7

反応物 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 69517063ethyl 6-chloro-7-[hydroxy(thien-2-yl)methyl]-2-(trifluoromethyl)-2H-chromene-3-carboxylate

生成物 1

HCID 69517825ethyl 6-chloro-7-(thien-2-ylmethyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

The crude oil from Example 170 Step 2 was dissolved in I mL of DCM. To this solution was added triethylsilane (41 μL, 0.26 mmol) and 20 μL of TFA and stirred at 25° C. After 24 h, the solution was stirred vigorously with solid NaHCO3 and H2O, which quenched the reaction. Stirring was stopped after 5 min, and the solution was allowed to separate into layers. The reaction mixture stood in this state for one day prior to workup. The organic layer was dried over MgSO4, filtered, and evaporated under reduced pressure to give an orange oil. The crude product was purified by flash chromatography to give reasonably pure compound.

後処理

  1. customquenched
  2. customthe reaction
  3. stirringStirring
  4. waitwas stopped after 5 min
  5. customto separate into layers
  6. waitThe reaction mixture stood in this state for one day
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customto give an orange oil
  11. customThe crude product was purified by flash chromatography
  12. customto give reasonably pure compound

出典と根拠

ORDレコード
ord-6564b16ceebd4588b55659a63816c4bf
出典データセット
uspto-grants-2007_08
特許番号
US07259266B2

反応ノート

読み込み中…