4-Methylmorpholine → HCID 58118959, 화합물

HRID 508154노트

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HRID 508154 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

HCID 58118959HCID 58118959, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

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온도
-10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9d88209e2aa5464bab63ea959074dc8a
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09095582B2

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