Ethyl Acetate → 1-(2-{4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl}-(E)-vinyl)-cycloheptanol

HRID 547034노트

반응식

HRID 547034 반응식
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[CH2:15]([C:17]([C:28]1[CH:33]=[CH:32][C:31]([C:34]#[C:35][C:36]2([OH:43])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)=[C:30]([CH3:44])[CH:29]=1)([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([CH3:27])[CH:21]=1)[CH2:18][CH3:19])[CH3:16].C(OCC)(=O)C>O1CCCC1.[Cl-].[Na+].O>[CH2:15]([C:17]([C:28]1[CH:33]=[CH:32][C:31](/[CH:34]=[CH:35]/[C:36]2([OH:43])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]2)=[C:30]([CH3:44])[CH:29]=1)([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([CH3:27])[CH:21]=1)[CH2:18][CH3:19])[CH3:16]

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 577090901-{4-[1-Ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenylethynyl}-cycloheptanol

생성물 1

HCID 577091051-(2-{4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl}-(E)-vinyl)-cycloheptanol수율 100.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

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온도
0 °C

실험 절차

Sodium bis(2-methoxyethoxy)aluminum hydride (65 wt % solution in toluene, 1.4 mL, 4.66 mmol) was added to a solution of 1-{4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenylethynyl}-cycloheptanol (Example 128-(1); 624 mg, 1.54 mmol) in tetrahydrofuran (7.5 mL) in a nitrogen atmosphere at 0° C., and the mixture was stirred at 0° C. for two hours. Brine and ethyl acetate were added to the reaction mixture, which was stirred for 20 minutes. Then, celite was added and the mixture was further stirred for 30 minutes. The mixture was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=90:10 to 50:50) to give the target compound as a colorless oil (629 mg, 100%).

후처리

  1. stirringwas stirred for 20 minutes
  2. additionThen, celite was added
  3. stirringthe mixture was further stirred for 30 minutes
  4. dry with materialThe mixture was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=90:10 to 50:50)

출처 및 근거

ORD 기록
ord-ddf9b763abd24f0faecaec7ee52e8d67
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935688B2

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