Water → 4-{1-Ethyl-1-(4-(3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl)-propyl}-2-methyl-phenol

HRID 546808ノート

反応式

HRID 546808 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([C:9]([C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([CH3:34])[CH:28]=1)([C:12]1[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:20]([CH2:24][CH3:25])([OH:23])[CH2:21][CH3:22])=[C:14]([CH3:26])[CH:13]=1)[CH2:10][CH3:11])[CH3:8].O>O1CCCC1>[CH2:7]([C:9]([C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([CH3:34])[CH:28]=1)([C:12]1[CH:17]=[CH:16][C:15]([CH:18]=[CH:19][C:20]([CH2:21][CH3:22])([OH:23])[CH2:24][CH3:25])=[C:14]([CH3:26])[CH:13]=1)[CH2:10][CH3:11])[CH3:8]

参加物

5

反応物 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 574329954-{1-Ethyl-1-(4-(3-ethyl-3-hydroxy-1-pentynyl)-3-methyl-phenyl)-propyl}-2-methyl-phenol

生成物 1

HCID 670650694-{1-Ethyl-1-(4-(3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl)-propyl}-2-methyl-phenol収率 62.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A 1 M solution of LiAlH4 in tetrahydrofuran (5.28 mL, 5.28 mmol) was added to a solution of 4-{1-ethyl-1-(4-(3-ethyl-3-hydroxy-1-pentynyl)-3-methyl-phenyl)-propyl}-2-methyl-phenol (Example 1-(4); 800 mg, 2.11 mmol) in tetrahydrofuran (8 mL) at room temperature. The mixture was heated under reflux for 18 hours and cooled, and then water was added. The mixture was filtered, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by a silica gel column (hexane/ethyl acetate=7/1) to give the title compound (500 mg, 62%).

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. temperaturecooled
  4. filtrationThe mixture was filtered
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by a silica gel column (hexane/ethyl acetate=7/1)

出典と根拠

ORDレコード
ord-055820622dac4e4085951c6f0aa58fea
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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