Methanol → HCID 15190010, compound

HRID 854152Notes

Reaction equation

HRID 854152 reaction equation
[C:1]([OH:6])(CC)(C)C.NC1C=CN=CC=1.[CH3:14][O:15][CH2:16][C@H:17]1[O:19][CH2:18]1.[C]=O.[CH3:22][OH:23]>>[CH3:22][O:23][C:1](=[O:6])[CH2:18][C@H:17]([OH:19])[CH2:16][O:15][CH3:14]

Participants

6

Reactant 5

HCID 887MethanolHCID 17274-AminopyridineHCID 64052-Methyl-2-butanolHCID 6992187(S)-(+)-Methyl glycidyl etherHCID 178418416HCID 178418416, compound

Product 1

HCID 15190010HCID 15190010, compoundYield 92%

Procedure

In a 50 mL-volumetric autoclave were added deaerated methanol (10 mL) and t-amyl alcohol (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 8 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 methyl ester (2.7 g, 92%, >99% ee) as a colorless oil.

Workup

  1. additionwas introduced
  2. customthe mixture was reacted at 40° C. for 8 hours
  3. customthe solvent was removed in vacuo
  4. distillationThe residue was subjected to Kugelrohr distillation

Sources & evidence

ORD record
ord-29de6db1c60a430aa58b0bc5d7131056
Source dataset
uspto-grants-2007_08
Patent number
US07256305B2

Reaction notes

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