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

HRID 854982노트

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HRID 854982 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6564b16ceebd4588b55659a63816c4bf
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259266B2

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