Triethylamine → (S)-glycidyl methanesulfonate

HRID 67284Notes

Reaction equation

HRID 67284 reaction equation
[CH2:1]1[O:3][C@@H:2]1[CH2:4][OH:5].C(N(CC)CC)C.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>C1(C)C=CC=CC=1>[S:14]([O:5][CH2:4][C@H:2]1[O:3][CH2:1]1)([CH3:13])(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5460455(+)-Glycidol

Product 1

HCID 12461090(S)-glycidyl methanesulfonateYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To an ice-cooled solution of (R)-glycidol (5.0 g, 0.068 m) and triethylamine (8.1 g, 0.080 m) in toluene (100 ml) was added, over 15 minutes, methanesulfonyl chloride (8.0 g, 0.070 m) in toluene (25 ml). Stirring was continued with cooling for 1 hour. The solution was filtered and concentrated to give an 80-85% yield of the crude (S)-3-mesyloxy-1,2-epoxypropane; this material could be used without further purification. Distillation gave 7 (61%); bp 92°-95° C./0.1 mm; [α]D22 =23.7° (c=5.16, CH3OH); 1H NMR (CDCl3) 4.5 (1H, d of d, J=12, J=3), 4.1 (1H, d of d, J=12, J=6), 3.3 (1H, m), 3.1 (3H, s), 2.8 (2H, m).

Workup

  1. additionwas added, over 15 minutes
  2. temperaturewith cooling for 1 hour
  3. filtrationThe solution was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6f0ace145ca440e1acddd378822572b8
Source dataset
uspto-grants-1982_08
Patent number
US04346042

Reaction notes

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