Pyridine → HCID 12019883, compound

HRID 2186896Notes

Reaction equation

HRID 2186896 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C@H:2]([CH3:4])[OH:3].N1C=CC=CC=1.Cl[C:16]([O:18][CH2:19][Cl:20])=[O:17]>C(OCC)C>[C:16](=[O:17])([O:3][C@H:2]([C:1]([O:6][CH2:7][CH3:8])=[O:5])[CH3:4])[O:18][CH2:19][Cl:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62754Chloromethyl chloroformateHCID 92831(L)-ethyl lactate

Product 1

HCID 12019883HCID 12019883, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To the mixture of ethyl (S)-lactate (23.6 g), pyridine (15.8 g) and diethyl ether (400 ml) was added dropwise a solution of chloromethyl chloroformate (25.6 g) in diethyl ether (100 ml) under ice cooling over the period of 40 minutes. After stirring at room temperature for 14 hours, the resulting solid was removed off by filtration. The filtrate was concentrated under reduced pressure and the residue was dissolved in ethyl acetate (250 ml). The solution was washed with water (150 ml×2) and a saturated sodium chloride aqueous solution (150 ml). After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain chloromethyl [(1S)-1-(ethoxycarbonyl)ethyl] carbonate (38.5 g) as a colorless liquid.

Workup

  1. customthe resulting solid was removed off by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate (250 ml)
  4. washThe solution was washed with water (150 ml×2)
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cd7b339600d84bf790f97b2973f840de
Source dataset
uspto-grants-2002_06
Patent number
US06407129B1

Reaction notes

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