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

HRID 546861ノート

反応式

HRID 546861 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-fd746b5cda4d43c49a8e37d9f6c5d7c9
出典データセット
uspto-grants-2011_05
特許番号
US07935688B2

反応ノート

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