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

HRID 2309134노트

반응식

HRID 2309134 반응식
[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

참가 물질

6

반응물 5

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-816a39d162bb4cf8af99d4f913107364
출처 데이터셋
uspto-grants-1987_09
특허 번호
US04692464

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