Sodium Hydroxide → (2s)-2-(Biphenyl-4-yloxy)-3-methylbutan-1-ol

HRID 379973Notes

Reaction equation

HRID 379973 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:12]=[CH:11][C:10]([O:13][C@@H:14]([CH:19]([CH3:21])[CH3:20])[C:15](OC)=[O:16])=[CH:9][CH:8]=1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.C(OCC)C.O>[C:7]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:12]=[CH:11][C:10]([O:13][C@@H:14]([CH:19]([CH3:21])[CH3:20])[CH2:15][OH:16])=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 131722882(2S)-2-(Biphenyl-4-yloxy)-3-methylbutyric acid, methyl ester

Product 1

HCID 57122588(2s)-2-(Biphenyl-4-yloxy)-3-methylbutan-1-ol

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium aluminium hydride (1.0M in tetrahydrofuran, 16 ml,) was added dropwise to a stirred (2S)-2-(biphenyl-4-yloxy)-3-methylbutyric acid, methyl ester (4.0 g, Example 8a)) in dry tetrahydrofuran (80 ml) at room temperature and the reaction was left to stir overnight. Water (0.6 ml), then aqueous sodium hydroxide (50%, 0.6 ml) then water (2.4 ml) were cautiously added to the solution at 0° C. Diethyl ether (200 ml) and anhydrous magnesium sulfate (10 g) were added and the solution stirred at room temperature for 10 minutes. The solution was filtered and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with dichloromethane then dichloromethane:ether (49:1) to give the sub-title compound as an oil which solidified on standing (3.43 g).

Workup

  1. waitthe reaction was left
  2. stirringthe solution stirred at room temperature for 10 minutes
  3. filtrationThe solution was filtered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was purified by column chromatography over silica eluting with dichloromethane

Sources & evidence

ORD record
ord-e168ed28f75247d3870c0069f38b185e
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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