Ethanol → HCID 58602418, compound

HRID 854147Notes

Reaction equation

HRID 854147 reaction equation
[CH2:1]([OH:3])C.N[C:5]1[CH:10]=CN=CC=1.[CH3:11][O:12][CH2:13][C@H:14]1[O:16][CH2:15]1.[C]=[O:18]>C1(C)C=CC=CC=1>[CH2:10]([O:18][C:1](=[O:3])[CH2:15][C@H:14]([OH:16])[CH2:13][O:12][CH3:11])[CH3:5]

Participants

6

Reactant 4

HCID 702EthanolHCID 17274-AminopyridineHCID 6992187(S)-(+)-Methyl glycidyl etherHCID 178418416HCID 178418416, compound

Product 1

HCID 58602418HCID 58602418, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 50 mL-volumetric autoclave were added deaerated ethanol (10 mL) and toluene (10 mL), and thereto were added 4-aminopyridine (47 mg, 0.5 mmol) and (S)-methylglycidyl ether (1.8 g, 20 mmol, >99% ee). Then to the mixture was added crystalline dicobaltoctacarbonyl complex (171 mg, 0.5 mmol). After covering the autoclave with a cap, carbon monoxide (1 MPa) was introduced therein and the mixture was reacted at 40° C. for 20 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was subjected to Kugelrohr distillation to give (S)-4-methoxy-3-hydroxybutanoic acid ethyl ester (3.0 g, 92%, >99% ee) as a colorless oil.

Workup

  1. additionwas introduced
  2. customthe mixture was reacted at 40° C. for 20 hours
  3. customthe solvent was removed in vacuo
  4. distillationThe residue was subjected to Kugelrohr distillation

Sources & evidence

ORD record
ord-46f90e8046c14d7c88ee696d0d3fa3b6
Source dataset
uspto-grants-2007_08
Patent number
US07256305B2

Reaction notes

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