(+-)-Pantolactone → Keto-pantoyllactone

HRID 399617

Reaction equation

HRID 399617 reaction equation
[CH3:1][C:2]1([CH3:9])[CH:7]([OH:8])[C:5](=[O:6])[O:4][CH2:3]1.ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O.C([O-])(=O)C.[Na+]>CC1(C)N([O])C(C)(C)CCC1.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:9])[C:7](=[O:8])[C:5](=[O:6])[O:4][CH2:3]1

Participants

6

Reactant 3

HCID 989(+-)-PantolactoneHCID 6909Trichloroisocyanuric AcidHCID 517045Sodium Acetate

Product 1

HCID 39Keto-pantoyllactoneYield 89.4%

Reagents, catalysts & solvents 2

HCID 2724126TempoCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.5 g (19.2 mmol) of pantolactone were reacted with 1.8 g (7.7 mmol) of trichloroisocyanuric acid in the presence of 30 mg (0.12 mmol) of TEMPO derivative C and 1.65g (20.1 mmol) of sodium acetate analogously to Example 14. In contrast to Example 14, ethyl acetate (20 ml) was used as the solvent. The reaction had finished after 2 hours. After recrystallization of the crude product there were obtained 2.2 g (89%) of ketopantolactone, m.p. 68°-69° C., GC content: 100% (area percent).

Workup

  1. customAfter recrystallization of the crude product

Sources & evidence

ORD record
ord-eabf6f8f96b0446daa31797acac3cb72
Source dataset
uspto-grants-1998_10
Patent number
US05821374

Linked notes

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