Methyl pivaloylacetate → 3,3-Dimethyl-1-[3-(3-nitrophenyl)-1,2,4-oxadiazol-5-yl]butan-2-one

HRID 916240ノート

反応式

HRID 916240 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7](=[N:9][OH:10])[NH2:8])([O-:3])=[O:2].[CH3:14][C:15]([CH3:24])([CH3:23])[C:16](=[O:22])[CH2:17][C:18](OC)=O>C1(C)C=CC=CC=1>[CH3:14][C:15]([CH3:24])([CH3:23])[C:16](=[O:22])[CH2:17][C:18]1[O:10][N:9]=[C:7]([C:6]2[CH:11]=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:8]=1

参加物

4

反応物 2

HCID 99597Methyl pivaloylacetateHCID 3781554N'-hydroxy-3-nitrobenzenecarboximidamide

生成物 1

HCID 166551323,3-Dimethyl-1-[3-(3-nitrophenyl)-1,2,4-oxadiazol-5-yl]butan-2-one収率 90%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

In a 250 ml flask, place 16 g (0.088 m) of 3-nitrobenzamidoxime (9a), 21.3 g (0.135 m) of methyl 4,4-dimethyl-3-oxovalerate (10a; R1=t-butyl), and 120 ml of toluene. Heat and stir the reaction mixture under reflux with a Dean-Stark trap for 23 hrs. Distill off toluene under a reduced pressure at 50-60° C. to thick oil. Add 60 ml of heptane to the oil with stirring, cool and stir at 0-5° C. for 30 min. Collect solid, wash with heptane, and dry in air to give 22.9 g (90%) of 5-(3,3-dimethyl-2-oxobutyl)-3-(3-nitrophenyl)-1,2,4-oxadiazole [Formula II: R1=t-butyl and R2=3-nitrophenyl].

後処理

  1. temperatureHeat
  2. temperatureunder reflux with a Dean-Stark trap for 23 hrs
  3. distillationDistill off toluene under a reduced pressure at 50-60° C. to thick oil
  4. additionAdd 60 ml of heptane to the oil
  5. stirringwith stirring
  6. temperaturecool
  7. stirringstir at 0-5° C. for 30 min
  8. customCollect solid
  9. washwash with heptane
  10. customdry in air

出典と根拠

ORDレコード
ord-8555f6ddb9b34f4fab9a9b9727427c95
出典データセット
uspto-grants-2007_09
特許番号
US07268235B2

反応ノート

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