Ethylene Glycol → (1R,5S,6S,7R)-3,3-Ethylenedioxy-7-benzoyloxy-6-hydroxymethylbicyclo[3,3,0]octane

HRID 2198813ノート

反応式

HRID 2198813 の反応式
[CH2:1]([OH:4])[CH2:2][OH:3].[C:5]1([CH3:15])[CH:10]=[CH:9][C:8](S(O)(=O)=O)=[CH:7][CH:6]=1.[CH:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:22](=[O:25])(O)[O-:23].[Na+].CC[O:29][CH2:30][CH3:31]>>[CH2:2]1[CH2:1][O:4][C:8]2([CH2:7][C@H:6]3[C@H:10]([CH2:5][C@@H:15]([O:23][C:22](=[O:25])[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C@@H:31]3[CH2:30][OH:29])[CH2:9]2)[O:3]1

参加物

6

反応物 5

HCID 174Ethylene GlycolHCID 241BenzeneHCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 516892Sodium Bicarbonate

生成物 1

HCID 22822073(1R,5S,6S,7R)-3,3-Ethylenedioxy-7-benzoyloxy-6-hydroxymethylbicyclo[3,3,0]octane

実験手順

320 mg. of the alcohol prepared according to Reference Example 1(o), 0.5 ml. of ethylene glycol, 4 mg. of p-toluenesulfonic acid, and 10 ml. of benzene are agitated for 1.5 hours with the use of a water trap at reflux temperature. The mixture is cooled, diluted with ether, shaken once with 4% sodium bicarbonate solution, washed neutral with water, dried over magnesium sulfate, and evaporated under vacuum, thus obtaining 390 mg. of the ketal as a colorless oil.

後処理

  1. temperatureat reflux temperature
  2. temperatureThe mixture is cooled
  3. washwashed neutral with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under vacuum
  6. customthus obtaining 390 mg

出典と根拠

ORDレコード
ord-5cdddd806c544030850fbf748023cc94
出典データセット
uspto-grants-1982_11
特許番号
US04359581

反応ノート

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