Pyridine → HCID 67079500, compound

HRID 1499988Notes

Reaction equation

HRID 1499988 reaction equation
[CH3:1][S:2]([CH2:5][CH:6]([OH:9])[CH2:7][OH:8])(=[O:4])=[O:3].N1C=CC=CC=1.C1(C)C=CC=CC=1.Cl[C:24](Cl)([O:26]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl.O>[CH3:1][S:2]([CH2:5][CH:6]1[CH2:7][O:8][C:24](=[O:26])[O:9]1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 1049PyridineHCID 1140TolueneHCID 94429TriphosgeneHCID 214129233-(Methanesulfonyl)propane-1,2-diol

Product 1

HCID 67079500HCID 67079500, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5.70 g (37.0 mmol) of 3-(methylsulfonyl)propane-1,2-diol and 17.56 g (220.0 mol) of pyridine were dissolved in 100 mL of methylene chloride, and 20 mL of a toluene solution of 10.97 g (37.0 mmol) of triphosgene was dropwise added to the solution at an inner temperature of from 5° C. to 15° C., taking 30 minutes, and stirred at room temperature for 1 hour. 20 mL of water was added thereto for liquid-liquid separation, and the organic layer was dried with magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from dimethyl carbonate/acetonitrile to give 1.30 g of the intended 4-(methylsulfonylmethyl)-1,3-dioxolan-2-one (yield 20%).

Workup

  1. customfor liquid-liquid separation
  2. dry with materialthe organic layer was dried with magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from dimethyl carbonate/acetonitrile

Sources & evidence

ORD record
ord-7bb096c9e7154ddaa2a00b764a45c22a
Source dataset
uspto-grants-2015_12
Patent number
US09203113B2

Reaction notes

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