1-Butanol → HCID 87556830, compound

HRID 854143Notes

Reaction equation

HRID 854143 reaction equation
N[C:2]1[CH:7]=[CH:6]N=C[CH:3]=1.[CH2:8]([O:10][CH2:11][C@@H:12]1[O:14][CH2:13]1)[CH3:9].[C]=[O:16].[CH2:17]([OH:21])CCC>>[CH2:3]([O:16][C:17](=[O:21])[CH2:13][C@@H:12]([OH:14])[CH2:11][O:10][CH2:8][CH3:9])[CH2:2][CH2:7][CH3:6]

Participants

5

Reactant 4

HCID 2631-ButanolHCID 17274-AminopyridineHCID 6994434HCID 6994434, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 87556830HCID 87556830, compoundYield 90%

Procedure

In a 50 mL-volumetric autoclave were added deaerated n-butanol (20 mL), and thereto were added 4-aminopyridine (47 mg, 0.5 mmol) and (R)-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 45° C. for 12 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was subjected to Kugelrohr distillation to give (R)-4-ethoxy-3-hydroxybutanoic acid n-butyl ester (3.7 g, 90%, >99% ee) as a colorless oil.

Workup

  1. additionwas introduced
  2. customthe mixture was reacted at 45° C. for 12 hours
  3. customthe solvent was removed in vacuo
  4. distillationThe residue was subjected to Kugelrohr distillation

Sources & evidence

ORD record
ord-f7cc5eba2060478ca856d7b32141a815
Source dataset
uspto-grants-2007_08
Patent number
US07256305B2

Reaction notes

Loading…