4-Methylmorpholine → HCID 58118959、化合物

HRID 508154ノート

反応式

HRID 508154 の反応式
[C:1]1([C:7]2[O:8][C:9]([C:15]([F:18])([F:17])[F:16])=[C:10]([C:12](O)=[O:13])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN1CCOCC1.ClC(OCC)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1.O>[C:1]1([C:7]2[O:8][C:9]([C:15]([F:17])([F:18])[F:16])=[C:10]([CH2:12][OH:13])[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

8

反応物 5

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 27764382-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 58118959HCID 58118959、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-10 °C

実験手順

500 mg (1.94 mmol) of 2-phenyl-5-(trifluoromethyl)-1,3-oxazole-4-carboxylic acid are dissolved in 40 ml of dry THF and cooled to −10° C. 197 mg (1.94 mmol) of 4-methylmorpholine and 211 mg (1.94 mmol) of ethyl chloroformate are added. The reaction solution is stirred at −10° C. for 1 h. 3.9 ml (3.89 mmol) of a 1 M solution of lithium aluminum hydride in THF are then slowly added dropwise. The reaction mixture is stirred overnight and slowly allowed to warm to RT. The mixture is then once more cooled to 0° C., and 0.6 ml of water and 1.2 ml of 1 N aqueous sodium hydroxide solution are added carefully. The mixture is then stirred at RT overnight. After filtration, the solvent is removed on a rotary evaporator. The residue is used without further purification in the subsequent reaction.

後処理

  1. stirringThe reaction mixture is stirred overnight
  2. temperatureto warm to RT
  3. temperatureThe mixture is then once more cooled to 0° C.
  4. stirringThe mixture is then stirred at RT overnight
  5. filtrationAfter filtration
  6. customthe solvent is removed on a rotary evaporator
  7. customThe residue is used without further purification in the subsequent reaction

出典と根拠

ORDレコード
ord-9d88209e2aa5464bab63ea959074dc8a
出典データセット
uspto-grants-2015_08
特許番号
US09095582B2

反応ノート

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