Sodium Chloride → (R)-4-(Oxiran-2-ylmethoxy)benzonitrile

HRID 345140Notes

Reaction equation

HRID 345140 reaction equation
[C:1]([C:3]1[CH:18]=[CH:17][C:6]([O:7][CH2:8][C@H:9]([OH:16])[CH2:10]OS(C)(=O)=O)=[CH:5][CH:4]=1)#[N:2].[OH-].[Na+].[Cl-].[Na+]>COCCOC>[O:16]1[CH2:10][C@@H:9]1[CH2:8][O:7][C:6]1[CH:17]=[CH:18][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 15066864(2S)-1-(4-cyanophenoxy)-3-methane-sulfonyloxypropan-2-ol

Product 1

HCID 6934186(R)-4-(Oxiran-2-ylmethoxy)benzonitrileYield 100.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 2.71 g of (2S)-1-(4-cyanophenoxy)-3-methanesulfonyloxypropan-2-ol in 40 ml of 1,2-dimethoxyethane was stirred with 1.0 g of powdered sodium hydroxide at room temperature for 22 h. 10 ml of saturated sodium chloride solution was added, and the mixture was extracted twice with ether. Washing with 5% sodium hydrogen carbonate, drying over magnesium sulfate, filtration and evaporation gave 1.76 g of crystalline material, m.p. 67.5° C., [α]D20 -14.7° (c=1, acetone)

Workup

  1. extractionthe mixture was extracted twice with ether
  2. washWashing with 5% sodium hydrogen carbonate
  3. dry with materialdrying over magnesium sulfate, filtration and evaporation

Sources & evidence

ORD record
ord-6502e50d01ff4812be887b12e6ecdaac
Source dataset
uspto-grants-1991_10
Patent number
US05055490

Reaction notes

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