(+-)-Pantolactone → Keto-pantoyllactone

HRID 399614

反応式

HRID 399614 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 39Keto-pantoyllactone収率 71.1%

試薬・触媒・溶媒 2

HCID 2724126Tempo触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-eb9f6d5bd4584a7e902f4f376752d67b
出典データセット
uspto-grants-1998_10
特許番号
US05821374

関連ノート

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