(+-)-Pantolactone → Keto-pantoyllactone

HRID 399614

반응식

HRID 399614 반응식
[OH:1][CH:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][O:5][C:3]1=[O:4].C([O-])(=O)C.[Na+].ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O>C(Cl)Cl.CC1(C)N([O])C(C)(C)CCC1>[CH3:8][C:7]1([CH3:9])[C:2](=[O:1])[C:3](=[O:4])[O:5][CH2:6]1

참가 물질

6

반응물 3

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

생성물 1

HCID 39Keto-pantoyllactone수율 71.1%

시약·촉매·용매 2

HCID 2724126Tempo촉매HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

5 g (38.4 mmol) of 2-hydroxy-3,3-dimethyl-γ-butyrolactone (pantolactone) were dissolved in 118 ml of methylene chloride in a 200 ml sulphonation flask. 3.3 g (40.2 mmol) of sodium acetate and 3.6 g (15.5 mmol) of trichloroisocyanuric acid were added thereto. The mixture was cooled to 0° C. while stirring. A solution of 60 mg (0.28 mmol) of TEMPO derative B in 2 ml of methylene chloride was dosed in within 10 minutes. The temperature was held at 0°-3° C. by constant cooling. The reaction had finished after 3 hours. The white precipitate was filtered off and the filtrate was treated with sodium bisulphite solution in order to reduce the excess trichloroisocyanuric acid. Working up of the reaction mixture and subsequent recrystallization of the crude product gave 3.5 g (71%) of ketopantolactone, GC content: 99.6% (area percent).

후처리

  1. customwas dosed in within 10 minutes
  2. customwas held at 0°-3° C. by constant cooling
  3. filtrationThe white precipitate was filtered off
  4. additionthe filtrate was treated with sodium bisulphite solution in order
  5. customWorking up of the reaction mixture and subsequent recrystallization of the crude product

출처 및 근거

ORD 기록
ord-eb9f6d5bd4584a7e902f4f376752d67b
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05821374

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