tert-Butyl hydroperoxide → 4-(trifluoromethyl)-6,6a-dihydro-1aH-indeno[1,2-b]oxirene

HRID 1191926노트

반응식

HRID 1191926 반응식
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][CH2:9]2)=[CH:5][CH:4]=1.C([O:18]O)(C)(C)C>ClCCl.CCCCCCCCCC.[Ti](Cl)(Cl)(Cl)Cl>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[CH:5][C:6]2[CH:7]3[O:18][CH:8]3[CH2:9][C:10]=2[CH:11]=1

참가 물질

6

반응물 2

HCID 6410tert-Butyl hydroperoxideHCID 190955106-(trifluoromethyl)-1H-indene

생성물 1

HCID 592126284-(trifluoromethyl)-6,6a-dihydro-1aH-indeno[1,2-b]oxirene

시약·촉매·용매 3

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매HCID 15600Decane용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 6-(trifluoromethyl)-1H-indene (1.1 g, 6 mmol) in anhydrous dichloromethane (80 mL) at −78° C. was added a 5.5 M solution of tert-butyl hydroperoxide in n-decane (1.3 mL) followed by titanium tetrachloride (0.79 mL, 7.2 mmol). After being stirred at −78° C. for 1 h, the resulting brown solution was quenched with a mixture of Et2O/saturated Na2SO3 solution. The mixture was stirred at ambient temperature for 1 h to give a colorless solution. The organic layer was separated and washed with brine, dried over MgSO4 and concentrated to give the crude product (1.2 g) as a solid. LC/MS calculated for C10H2F3O: (M+H)+ 201. found 201.0.

후처리

  1. customthe resulting brown solution was quenched with a mixture of Et2O/saturated Na2SO3 solution
  2. stirringThe mixture was stirred at ambient temperature for 1 h
  3. customto give a colorless solution
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d9601e30fdaf46fb855cf8c62d9b7fe3
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680104B2

반응 노트

불러오는 중…