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Potassium Hydroxide → Acyclic retinoid

HRID 1611061
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HRID 1611061 반응식
[OH-].[K+].[CH3:3]/[C:4](/[CH:11]=[CH:12]/[CH:13]=[C:14](\[CH3:26])/[CH2:15][CH2:16]/[CH:17]=[C:18](\[CH3:25])/[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[CH:5]\[C:6]([O:8]CC)=[O:7]>CC(O)C>[CH3:3]/[C:4](/[CH:11]=[CH:12]/[CH:13]=[C:14](\[CH3:26])/[CH2:15][CH2:16]/[CH:17]=[C:18](\[CH3:25])/[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[CH:5]\[C:6]([OH:8])=[O:7]
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참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 11984134Ethyl (2E,4E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,4,6,10,14-pentaenoate

생성물 1

HCID 6437836Acyclic retinoid수율 51%

시약·촉매·용매 1

HCID 3776Isopropanol용매2회

실험 절차

Potassium hydroxide (3.0 g) was dissolved in 20 ml of 2-propanol at 100° C. The solution was added with 2-propanol (10 ml) solution of ethyl (2E,4E,6E,10E)-3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoate obtained in Example 1, and stirred at the same temperature for 5 minutes. The reaction mixture was added to ice-water and washed with n-hexane. The solution was neutralized with 10% hydrochloric acid and extracted with n-hexane. The resulting organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was recrystallized from methanol to obtain 3.5 g of the title compound (yield 51%) as a yellow crystal.

후처리

  1. washwashed with n-hexane
  2. extractionextracted with n-hexane
  3. washThe resulting organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was recrystallized from methanol

출처 및 근거

ORD 기록
ord-e9886ed1a69f4156afd31277a8ccb8cb
출처 데이터셋
uspto-grants-2006_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06984742B2

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