Water → 9,10-Dimethylene-11-oxa-tricyclo[5.3.1.01,5]undecane

HRID 10904ノート

反応式

HRID 10904 の反応式
C(OCC)C.O[CH:7]([CH2:15][C:16]([CH2:19][Si](C)(C)C)=[C:17]=[CH2:18])[CH2:8][CH:9]1[CH2:13][CH2:12][CH2:11][C:10]1=[O:14].[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.O>CCOC(C)=O>[CH2:19]=[C:16]1[C:17](=[CH2:18])[C:10]23[O:14][CH:7]([CH2:8][CH:9]2[CH2:13][CH2:12][CH2:11]3)[CH2:15]1

参加物

6

反応物 4

HCID 962WaterHCID 3283Diethyl EtherHCID 65367Trimethylsilyl triflateHCID 121566812-(2-Hydroxy-4-trimethylsilanylmethyl-hexa-4,5-dienyl)-cyclopentanone

生成物 1

HCID 112867759,10-Dimethylene-11-oxa-tricyclo[5.3.1.01,5]undecane収率 78.6%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

1.1 mL of diethyl ether was added to 2-(2-hydroxy-4-trimethylsilanylmethyl-hexa-4,5-dienyl)-cyclopentanone (70 mg, 0.26 mmol) under nitrogen atmosphere. While stirring at −78° C., TMSOTf (48 μL, 0.26 mmol) was added. While stirring the reaction mixture, the reaction temperature was slowly increased to room temperature for 3 hours. The reaction mixture was stirred at room temperature for 30 minutes. After the reaction was completed, H2O was added. After stirring for about 5 minutes, the reaction mixture was diluted with EtOAc and washed with water and saturated brine. The organic layer was separated from the reaction mixture and dried with anhydrous MgSO4. The solvent was removed under reduced pressure and the remaining material was purified with column chromatography (EtOAc/n-hexane=1/15) to obtain 36 mg of the product (77%).

後処理

  1. stirringWhile stirring the reaction mixture
  2. temperaturethe reaction temperature was slowly increased to room temperature for 3 hours
  3. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  4. stirringAfter stirring for about 5 minutes
  5. washwashed with water and saturated brine
  6. customThe organic layer was separated from the reaction mixture
  7. dry with materialdried with anhydrous MgSO4
  8. customThe solvent was removed under reduced pressure
  9. customthe remaining material was purified with column chromatography (EtOAc/n-hexane=1/15)

出典と根拠

ORDレコード
ord-a7a75a81d0d140da93aa04a74ed8d4fd
出典データセット
uspto-grants-2006_08
特許番号
US07094913B2

反応ノート

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