Ethanol → HCID 87556526, compound

HRID 854142Notes

Reaction equation

HRID 854142 reaction equation
[CH2:1]([OH:3])C.N[C:5]1[CH:10]=CN=CC=1.[CH2:11]([O:13][CH2:14][C@H:15]1[O:17][CH2:16]1)[CH3:12].[C]=[O:19]>C1(C)C=CC=CC=1>[CH2:10]([O:19][C:1](=[O:3])[CH2:16][C@H:15]([OH:17])[CH2:14][O:13][CH2:11][CH3:12])[CH3:5]

Participants

6

Reactant 4

HCID 702EthanolHCID 17274-AminopyridineHCID 6999880HCID 6999880, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 87556526HCID 87556526, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 50 mL-volumetric autoclave were added deaerated ethanol (10 mL) and toluene, and thereto were added 4-aminopyridine (47 mg, 0.5 mmol) and (S)-ethylglycidyl ether (2.0 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 18 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was subjected to Kugelrohr distillation to give (S)-4-ethoxy-3-hydroxybutanoic acid ethyl ester (3.0 g, 85%, >99% ee) as a colorless oil.

Workup

  1. additionwas introduced
  2. customthe mixture was reacted at 40° C. for 18 hours
  3. customthe solvent was removed in vacuo
  4. distillationThe residue was subjected to Kugelrohr distillation

Sources & evidence

ORD record
ord-8023941f89c8432aab1988f22976acf7
Source dataset
uspto-grants-2007_08
Patent number
US07256305B2

Reaction notes

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