Sodium Hydroxide → HCID 54094447, compound

HRID 379962Notes

Reaction equation

HRID 379962 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:12]=[CH:11][C:10]([O:13][C@H:14]([CH3:20])[C:15](OCC)=[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:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:8]=[CH:9][C:10]([O:13][C@H:14]([CH3:20])[CH2:15][OH:16])=[CH:11][CH:12]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 71354157HCID 71354157, compound

Product 1

HCID 54094447HCID 54094447, compoundYield 94.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (86.67 ml, 1.0 M solution in tetrahydrofuran) was added dropwise to a stirred solution of (2R)-2-(biphenyl-4-yloxy)propanoic acid, ethyl ester (11.79 g, Example 1a) in dry tetrahydrofuran (200 ml) at 0° C. The resulting solution was stirred at room temperature under nitrogen for 3 hours. Water (3.3 ml), then aqueous sodium hydroxide (50% solution, 3.3 ml) then water (9.9 ml) were cautiously added to the solution at 0° C. Diethyl ether (200 ml) and anhydrous magnesium sulfate (20 g) were added and the solution stirred at room temperature for 20 minutes. The solution was filtered and the filtrate concentrated under reduced pressure to give the sub-title compound as a solid (9.43 g).

Workup

  1. stirringthe solution stirred at room temperature for 20 minutes
  2. filtrationThe solution was filtered
  3. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-8e810a7563d04df6b4eaf003a39eea73
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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