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

HRID 547034ノート

反応式

HRID 547034 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-ddf9b763abd24f0faecaec7ee52e8d67
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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