2-Trimethylsilyl-1,3-dithiane → 2-(6-{4-n-Propylcyclohexyl}spiro[3.3]hept-2-ylidene)[1,3]dithiane

HRID 916530

반응식

HRID 916530 반응식
C[Si](C)(C)[CH:3]1[S:8][CH2:7][CH2:6][CH2:5][S:4]1.[Li]CCCC.[CH2:16]([CH:19]1[CH2:24][CH2:23][CH:22]([CH:25]2[CH2:32][C:27]3([CH2:30][C:29](=O)[CH2:28]3)[CH2:26]2)[CH2:21][CH2:20]1)[CH2:17][CH3:18]>C1COCC1>[CH2:16]([CH:19]1[CH2:20][CH2:21][CH:22]([CH:25]2[CH2:32][C:27]3([CH2:30][C:29](=[C:3]4[S:8][CH2:7][CH2:6][CH2:5][S:4]4)[CH2:28]3)[CH2:26]2)[CH2:23][CH2:24]1)[CH2:17][CH3:18]

참가 물질

5

반응물 3

HCID 834132-Trimethylsilyl-1,3-dithianeHCID 193876012-(trans-4-Propylcyclohexyl)spiro[3.3]heptan-6oneHCID 178418339Butyllithium

생성물 1

HCID 585962542-(6-{4-n-Propylcyclohexyl}spiro[3.3]hept-2-ylidene)[1,3]dithiane

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-70 °C

실험 절차

15.5 g (80.3 mmol) of 2-trimethylsilyl-1,3-dithiane are dissolved in 150 ml of THF, and 51 ml (80.3 mmol) of n-BuLi (15 percent in hexane) are rapidly added dropwise at −70° C. The batch is subsequently allowed to thaw to 0° C. over the course of 4 hours, stirred for 10 minutes without cooling and re-cooled to −70° C., and a solution of 17.0 g (72.5 mmol) of 6-(4-n-propylcyclohexyl)spiro[3.3]heptan-2-one 5 in 50 ml of THF is added drop-wise. The batch is left to stir overnight at room temperature, hydrolysed using saturated sodium hydrogencarbonate solution and extracted with dichloromethane. The combined organic phases are washed with water and dried over sodium sulfate. The solvent is removed under reduced pressure, and the crude product is recrystallised from n-heptane. The dithioacetal 6 is obtained as colourless flakes.

후처리

  1. customthaw to 0° C.
  2. customover the course of 4 hours
  3. temperaturewithout cooling
  4. waitThe batch is left
  5. stirringto stir overnight at room temperature
  6. extractionhydrolysed using saturated sodium hydrogencarbonate solution and extracted with dichloromethane
  7. washThe combined organic phases are washed with water
  8. dry with materialdried over sodium sulfate
  9. customThe solvent is removed under reduced pressure
  10. customthe crude product is recrystallised from n-heptane

출처 및 근거

ORD 기록
ord-02150b853006410f8c6b73682c2e4987
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07270856B2

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