Citric Acid → 2-[1-[2-(3,5-Diacetoxymethylphenyoxy)ethyl]cyclohexyl]ethanol

HRID 2223910노트

반응식

HRID 2223910 반응식
[O:1]([CH2:19][CH2:20][C:21]1([CH2:27][CH2:28][O:29][C:30]2[CH:35]=[C:34]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[CH:33]=[C:32]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[CH:31]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[C:38]([O:37][CH2:36][C:34]1[CH:35]=[C:30]([O:29][CH2:28][CH2:27][C:21]2([CH2:20][CH2:19][OH:1])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[CH:31]=[C:32]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[CH:33]=1)(=[O:40])[CH3:39]

참가 물질

5

반응물 3

HCID 311Citric AcidHCID 11078149TBAF tetrahydrofuranHCID 691465871-[2-[1-[2-(Tert-butyldiphenylsiloxy)ethyl]cyclohexyl]ethoxy]-3,5-diacetoxymethylbenzene

생성물 1

HCID 597148422-[1-[2-(3,5-Diacetoxymethylphenyoxy)ethyl]cyclohexyl]ethanol수율 62.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-[2-[1-[2-(tert-butyldiphenylsiloxy)ethyl]cyclohexyl]ethoxy]-3,5-diacetoxymethylbenzene (1.13 g) dissolved in tetrahydrofuran (7 mL) was added a 1M tetrabutylammonium fluoride/tetrahydrofuran solution (2.8 mL) dropwise at room temperature. The solution was stirred for 15 hours. A 10% aqueous citric acid solution was added to the solution, and it was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was then concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, hexane:ethyl acetate (1:1)] to give the title compound (439 mg).

후처리

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was then concentrated under reduced pressure
  6. customThe resulting residue was purified by chromatography [silica gel, hexane:ethyl acetate (1:1)]

출처 및 근거

ORD 기록
ord-d06f058558e0464c92bac6474ccdea20
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07375115B2

반응 노트

불러오는 중…