Keto-pantoyllactone → D-Pantolactone

HRID 704097

Reaction equation

HRID 704097 reaction equation
[CH3:1][C:2]1([CH3:9])[C:7](=[O:8])[C:5](=[O:6])[O:4][CH2:3]1.[H][H]>C1COCC1>[CH3:1][C:2]1([CH3:9])[C@@H:7]([OH:8])[C:5](=[O:6])[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 39Keto-pantoyllactoneHCID 178418361HCID 178418361, compound

Product 1

HCID 439368D-Pantolactone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

0.0025 m-mole of rhodium-1,5-cyclooctadienechloride complex and 0.0065 m-mole of one of the asymmetric ligand compounds indicated in Table 2 were dissolved in 10 ml of THF, and 5 m-mole of ketopantolactone was added thereto. Reduction was carried out at a hydrogen atmosphere of 50 atm. The mixture was stirred at 50° C. for 45 hours. The reaction mixture was concentrated under reduced pressure and distilled under reduced pressure to obtain optically active (R)-(-)pantolactone. The results are shown in Table 2.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-92b04c10ec5244d78ceb50444da25eac
Source dataset
uspto-grants-1991_01
Patent number
US04985567

Linked notes

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