Methanol → 3-Carboxymethyl-5-(3-fluoro-4-phenyl-alpha-methylbenzyl)-1,2,4-oxadiazole

HRID 2290771ノート

反応式

HRID 2290771 の反応式
[C:1]([CH2:3][C:4]1[N:8]=[C:7]([CH:9]([CH3:23])[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:12]([F:22])[CH:11]=2)[O:6][N:5]=1)#N.[OH-:24].[K+].C[OH:27]>O>[C:1]([CH2:3][C:4]1[N:8]=[C:7]([CH:9]([CH3:23])[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:12]([F:22])[CH:11]=2)[O:6][N:5]=1)([OH:27])=[O:24]

参加物

5

反応物 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 136909683-Cyanomethyl-5-(3-fluoro-4-phenyl-alpha-methylbenzyl)-1,2,4-oxadiazole

生成物 1

HCID 136909693-Carboxymethyl-5-(3-fluoro-4-phenyl-alpha-methylbenzyl)-1,2,4-oxadiazole

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

To a solution of 1.4 g of 3-cyanomethyl-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole obtained in Example 38 in 50 ml of methanol was added a solution of 2.56 g of potassium hydroxide in 23 g of water. After stirring under reflux for 4 hours, the reaction mixture was cooled, diluted with water and extracted with chloroform. The organic phase was washed with water, dried over sodium sulfate and evaporated. The residue was chromatographed over silica gel using chloroformmethanol (20:1, v/v) to give 1.35 g of 3-carboxymethyl-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole as an oil. It was crystallized from diisopropyl ether to give colorless fine needles, m.p. 100.5°-101.5° C.

後処理

  1. temperatureunder reflux for 4 hours
  2. temperaturethe reaction mixture was cooled
  3. extractionextracted with chloroform
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was chromatographed over silica gel using chloroformmethanol (20:1

出典と根拠

ORDレコード
ord-db7455bdb2cf4748826b194a4ae5ae2a
出典データセット
uspto-grants-1986_10
特許番号
US04618617

反応ノート

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