Water → HCID 15549883, compound

HRID 975275Notes

Reaction equation

HRID 975275 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. MS(m/z): 142(M+) IR(neat,cm-1): 1750

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-5dc9f28dfb154891b41fa50ad3966b7d
Source dataset
uspto-grants-1997_03
Patent number
US05608073

Reaction notes

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