3-Nitrobenzenesulfonyl chloride → (Oxiran-2-yl)methyl 3-nitrobenzene-1-sulfonate

HRID 1596431Notes

Reaction equation

HRID 1596431 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH2:14]1[O:16][C@@H:15]1[CH2:17][OH:18]>>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([O:18][CH2:17][CH:15]2[CH2:14][O:16]2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 84763-Nitrobenzenesulfonyl chlorideHCID 5460455(+)-Glycidol

Product 1

HCID 286836(Oxiran-2-yl)methyl 3-nitrobenzene-1-sulfonateYield 97%

Conditions

Temperature
-20 °C

Procedure

m-Nitrobenzensulfonylchloride (12.6 g; 57 mmol) was added to a cold (−20° C.) solution of (R)-(+)-glycidol (5.5 g; 74 mmol) and TEA (10.3 mL; 74 mmol). The reaction mixture was stirred at −20° C. for 96 h. The solution was filtered and the filtrate washed with tartaric acid (10% w/w), brine, H2O and concentrated giving the title compound in a 97% yield.

Workup

  1. filtrationThe solution was filtered
  2. washthe filtrate washed with tartaric acid (10% w/w), brine, H2O
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f92cedc3ba064876a493bb29ecb75868
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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