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

HRID 546808노트

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HRID 546808 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-055820622dac4e4085951c6f0aa58fea
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935688B2

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