Sodium bis(2-methoxyethoxy)aluminiumhydride → 4-(1-ethyl-1-{4-[(E)-2-(1-hydroxy-cyclopentyl)-vinyl]-3-methyl-phenyl}-propyl)-2-methyl-phenol

HRID 546861노트

반응식

HRID 546861 반응식
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[CH2:15]([C:17]([C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[C:37]([CH3:42])[CH:36]=1)([C:20]1[CH:25]=[CH:24][C:23]([C:26]#[C:27][C:28]2([OH:33])[CH2:32][CH2:31][CH2:30][CH2:29]2)=[C:22]([CH3:34])[CH:21]=1)[CH2:18][CH3:19])[CH3:16]>O1CCCC1.C(OCC)(=O)C.[Cl-].[Na+].O>[CH2:15]([C:17]([C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[C:37]([CH3:42])[CH:36]=1)([C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]2([OH:33])[CH2:32][CH2:31][CH2:30][CH2:29]2)=[C:22]([CH3:34])[CH:21]=1)[CH2:18][CH3:19])[CH3:16]

참가 물질

6

반응물 2

HCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 574833964-{1-Ethyl-1-[4-(1-hydroxy-cyclopentylethynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenol

생성물 1

HCID 574629914-(1-ethyl-1-{4-[(E)-2-(1-hydroxy-cyclopentyl)-vinyl]-3-methyl-phenyl}-propyl)-2-methyl-phenol수율 92.8%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

Sodium bis(2-methoxyethoxy)aluminum hydride (3.33 M solution in toluene, 6.7 mL, 22.3 mmol) was added to a solution of 4-{1-ethyl-1-[4-(1-hydroxy-cyclopentylethynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenol (Example 32-(1); 2.8 g, 7.4 mmol) in tetrahydrofuran (37 mL) at 0° C., and the mixture was stirred at the same temperature for four hours. The reaction mixture was diluted with ethyl acetate. Brine and celite were added, and the mixture was stirred at room temperature for 30 minutes. The organic layer was dried over anhydrous magnesium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane only to hexane/ethyl acetate=3/1) to give the title compound (2.6 g, 92%).

후처리

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (hexane only to hexane/ethyl acetate=3/1)

출처 및 근거

ORD 기록
ord-fd746b5cda4d43c49a8e37d9f6c5d7c9
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935688B2

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