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

HRID 546808Notes

Reaction equation

HRID 546808 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-055820622dac4e4085951c6f0aa58fea
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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