(+-)-Pantolactone → Keto-pantoyllactone

HRID 399615

Reaction equation

HRID 399615 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>CC1(C)N([O])C(C)(C)CCC1>[CH3:1][C:2]1([CH3:9])[C:7](=[O:8])[C:5](=[O:6])[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 989(+-)-PantolactoneHCID 6909Trichloroisocyanuric Acid

Product 1

HCID 39Keto-pantoyllactoneYield 93.5%

Reagents, catalysts & solvents 1

HCID 2724126TempoCatalyst

Procedure

5 g (38.4 mmol) of pantolactone were reacted with 3.6 g (15.5 mmol) of trichloroisocyanuric acid as described in Example 13. In contrast to Example 13, 60 mg (0.25 mmol) of TEMPO derivative C were used as the catalyst. The reaction had finished after 3 hours. After recrystallization of the crude product there were obtained 4.6 g (93%) of ketopantolactone, m.p. 69°-70° C., GC content: 100% (area percent).

Workup

  1. customAfter recrystallization of the crude product

Sources & evidence

ORD record
ord-05d2bc7a176a47628cfe714f094b364a
Source dataset
uspto-grants-1998_10
Patent number
US05821374

Linked notes

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