Water → (3R*,4R*)-3,4-epoxy-2,2-dimethyl-7-nitro-3-chromanol

HRID 505648ノート

反応式

HRID 505648 の反応式
[CH3:1][C:2]1([CH3:15])[CH:7]=[CH:6][C:5]2[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:4]=2[O:3]1.CN1C=CN=C1.Cl[O-].[Na+].S([O-])([O-])(=[O:27])=S.[Na+].[Na+].[OH2:32]>C(OCC)(=O)C>[O:32]1[C@H:6]2[C@:7]1([OH:27])[C:2]([CH3:15])([CH3:1])[O:3][C:4]1[C:5]2=[CH:8][CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1

参加物

7

反応物 5

HCID 962WaterHCID 13901-MethylimidazoleHCID 24477Sodium ThiosulfateHCID 132228872,2-Dimethyl-7-nitro-2h-1-benzopyranHCID 23665760Sodium Hypochlorite

生成物 1

HCID 86761162(3R*,4R*)-3,4-epoxy-2,2-dimethyl-7-nitro-3-chromanol収率 66%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2,2-dimethyl-7-nitrobenzopyran (11.1 g, 53.9 mmol) in ethyl acetate (165 mL), (Cyc, Ph)-salen manganese complex (XX) (405 mg, 0.431 mmol) and N-methyl imidazole (858 μL, 10.8 mmol) were added, and sodium hypochlorite aqueous solution (101 g, 162 mmol) was added dropwise at 20° C. thereto over 15 minutes. After stirring the resulting mixture at room temperature for 3 hours, saturated sodium thiosulfate aqueous solution was added thereto under cooling with water. The resulting reaction solution was filtered through celite, the organic phase was washed with saturated sodium thiosulfate aqueous solution and saturated sodium chloride solution, and then dried over magnesium sulfate, and concentrated under a reduced pressure. The resulting solid was recrystallized in ethanol to obtain (3R*,4R*)-3,4-epoxy-2,2-dimethyl-7-nitro-3-chromanol (yield: 66%).

後処理

  1. customThe resulting reaction solution
  2. filtrationwas filtered through celite
  3. washthe organic phase was washed with saturated sodium thiosulfate aqueous solution and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customThe resulting solid was recrystallized in ethanol

出典と根拠

ORDレコード
ord-e392a0e5e27e458ab8bdd91aa9283013
出典データセット
uspto-grants-2010_08
特許番号
US07781483B2

反応ノート

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