Sodium Methoxide → HCID 12916445, compound

HRID 582895Notes

Reaction equation

HRID 582895 reaction equation
Cl[CH:2]([C@H:7]([OH:10])[CH2:8][CH3:9])[C:3]([O:5][CH3:6])=[O:4].C[O-].[Na+]>CO>[O:10]1[C@H:7]([CH2:8][CH3:9])[C@H:2]1[C:3]([O:5][CH3:6])=[O:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 54420244HCID 54420244, compound3×

Product 1

HCID 12916445HCID 12916445, compoundYield 82.87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To 130 ml of a methanol solution of 25.5 g (0.153 mol) of the methyl (3R)-2-chloro-3-hydroxypentanoate obtained in (2) above was added dropwise 30 g (0.155 mol) of a 28% methanol solution of sodium methoxide at 0 to 5° C., followed by stirring at room temperature for 1 hour. After confirming disappearance of the methyl (3R)-2-chloro-3-hydroxypentanoate by TLC, methanol was evaporated. The concentrate was cooled, adjusted to pH 8 to 9 with 120 ml of a phosphate buffer, and extracted with 300 ml of isopropyl ether. The isopropyl ether was evaporated, and the residue was purified by column chromatography to give 16.5 g (0.126 mol; yield: 82.87%) of the title compound.

Workup

  1. customwas evaporated
  2. temperatureThe concentrate was cooled
  3. extractionextracted with 300 ml of isopropyl ether
  4. customThe isopropyl ether was evaporated
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5f6971093e0d4e9889f0a5e8d3f9f2e1
Source dataset
uspto-grants-1999_07
Patent number
US05925792

Reaction notes

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