Triethylamine → (+)-Glycidol

HRID 1903712Notes

Reaction equation

HRID 1903712 reaction equation
[CH2:1]1[O:3][C@H:2]1[CH2:4][OH:5].C(N(CC)CC)C.[N+](C1C=CC=CC=1S(Cl)(=O)=O)([O-])=O>C1(C)C=CC=CC=1>[CH2:1]1[O:3][C@@H:2]1[CH2:4][OH:5].[CH2:1]1[O:3][C@H:2]1[CH2:4][OH:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 6973630(-)-Glycidol

Product 2

HCID 5460455(+)-GlycidolHCID 6973630(-)-Glycidol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

One gram of (R) or (S)-glycidol was dissolved in 20 ml of anhydrous toluene, and 2 ml of triethylamine was added. The mixture was cooled with ice, and 2.79 g of o-nitrobenzenesulfonyl chloride was added with stirring in three portions at an interval of 10 minutes. The mixture was further stirred for 1 hour with ice cooling. After the reaction, the insoluble materials were removed by filtration. The filtrate was concentrated at below 30° C., and the residue was charged onto a column of silica gel. The column was developed with benzene/ethyl acetate (10/1) to give 1.9 g of (S)-compound from (R)-glycidol, and 2.54 g of (R)-compound from (S)-glycidol.

Workup

  1. additionwas added
  2. stirringThe mixture was further stirred for 1 hour with ice cooling
  3. customAfter the reaction
  4. customthe insoluble materials were removed by filtration
  5. concentrationThe filtrate was concentrated at below 30° C.
  6. additionthe residue was charged onto a column of silica gel

Sources & evidence

ORD record
ord-a12ff99eb8484dd383e53ddcb20a75f0
Source dataset
uspto-grants-1984_03
Patent number
US04438107

Reaction notes

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