Water → HCID 15549883, compound

HRID 1082187Notes

Reaction equation

HRID 1082187 reaction equation
[CH:1]1([C@@H:4]([OH:21])[C@H:5](OS(C2C=CC(C)=CC=2)(=O)=O)[C:6]([O:8][CH3:9])=[O:7])[CH2:3][CH2:2]1.O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:1]1([C@H:4]2[O:21][C@H:5]2[C:6]([O:8][CH3:9])=[O:7])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 15549882HCID 15549882, compound

Product 1

HCID 15549883HCID 15549883, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2.97 g of methyl (2S,3R)-3-cyclopropyl-3-hydroxy-2-(p-toluenesulfonyloxy)propionate in 50 ml of acetonitrile are added 10.86 ml of water and 3.96 g of potassium carbonate successively at room temperature. Then, the reaction mixture is stirred at 50° C. for 2 days. The reaction mixture is cooled to room temperature, and insoluble materials are removed by filtration. The filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; diethylether) to give methyl (2R,3R)-3-cyclopropyl-2,3-epoxypropionate quantitatively.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. custominsoluble materials are removed by filtration
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customThe residue is purified by silica gel column chromatography (solvent; diethylether)

Sources & evidence

ORD record
ord-ce87c9106579438bb8075e767e85f0fd
Source dataset
uspto-grants-1996_12
Patent number
US05589502

Reaction notes

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