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

HRID 916530

反応式

HRID 916530 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-02150b853006410f8c6b73682c2e4987
出典データセット
uspto-grants-2007_09
特許番号
US07270856B2

関連ノート

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