Sodium Hydroxide → 3-Isopropyl-1,2,4-oxadiazole-5-carboxylic acid

HRID 1409317ノート

反応式

HRID 1409317 の反応式
[CH:1]([C:4]1[N:8]=[C:7]([C:9]([O:11]CC)=[O:10])[O:6][N:5]=1)([CH3:3])[CH3:2].[OH-].[Na+]>CCO.O>[CH:1]([C:4]1[N:8]=[C:7]([C:9]([OH:11])=[O:10])[O:6][N:5]=1)([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 534046373-Isopropyl-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester

生成物 1

HCID 232010263-Isopropyl-1,2,4-oxadiazole-5-carboxylic acid収率 102.8%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

Ethyl 3-isopropyl-1,2,4-oxadiazole-5-carboxylate (10.42 mmol, 1.919 g) was dissolved in EtOH (20 ml). Sodium hydroxide pellets (12.50 mmol, 0.500 g) were dissolved in cold water (10 ml) and solution slowly added. The resulting solution was heated at 60° C. for 1.5 h. EtOH was removed under vacuum. The residue was diluted with tert-butyl methyl ether. The mixture was acidified under cold conditions by adding 2 N HCl solution. The mixture was stirred overnight and washed with DCM. Water phase was evaporated precipitating the product. 1.673 g of the title compound was obtained. 1H-NMR (400 MHz, D2O): δ 1.33 (d, 6H), 3.10-3.25 (m, 1H).

後処理

  1. additionsolution slowly added
  2. customEtOH was removed under vacuum
  3. additionThe residue was diluted with tert-butyl methyl ether
  4. additionby adding 2 N HCl solution
  5. washwashed with DCM
  6. customWater phase was evaporated
  7. customprecipitating the product

出典と根拠

ORDレコード
ord-9e595cb122c241f99bd546075d4fb8e3
出典データセット
uspto-grants-2014_12
特許番号
US08921378B2

反応ノート

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