Tetrahydrofuran → Ethyl gamma-cyano-gamma-[3-(trifluoromethyl)phenyl]-4-morpholinebutanoate

HRID 903453노트

반응식

HRID 903453 반응식
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([CH:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.O1CCCC1.[C:25]([O:29][CH2:30][CH3:31])(=[O:28])[CH:26]=[CH2:27]>[OH-].[K+].C(O)C>[C:10]([C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:18])[F:19])[CH:4]=1)([N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)[CH2:27][CH2:26][C:25]([O:29][CH2:30][CH3:31])=[O:28])#[N:11]

참가 물질

6

반응물 3

HCID 8028TetrahydrofuranHCID 8821Ethyl Acrylate2회HCID 36941922-Morpholino-2-[3-(trifluoromethyl)phenyl]acetonitrile

생성물 1

HCID 12449509Ethyl gamma-cyano-gamma-[3-(trifluoromethyl)phenyl]-4-morpholinebutanoate

시약·촉매·용매 2

HCID 14797Potassium Hydroxide촉매2회HCID 702Ethanol용매2회

실험 절차

To a solution of 5.0 g. of α-[3-(trifluoromethyl)phenyl]-4-morpholineacetonitrile in 200 ml. of tetrahydrofuran stirred at room temperature is added 30 drops of 30% potassium hydroxide in ethanol. To the mixture is added 10 ml. of ethyl acrylate. After one hour an additional 30 drops of 30% potassium hydroxide in ethanol and 10 ml. of ethyl acrylate is added. The mixture is stirred for 2 hours and the solvent removed under vacuum. Toluene is added several times and the solvent removed. The residue is stirred with ether, filtered and the solvent evaporated to give ethyl γ-cyano-γ-[3-(trifluoromethyl)phenyl]-4-morpholinebutanoate (5.6 g.) as an oil. The oil is heated with 70% glacial acetic acid for 2 hours and the solvent removed. The residue is dissolved in dichloromethane and washed with water. The organic layer is dried (Na2SO4) and the solvent removed to give an oil. A mixture of the oil and 300 ml. of 6 N hydrochloric acid is refluxed for 5 hours, cooled and extracted with dichloromethane. The organic layer is extracted with sodium bicarbonate. The aqueous layer is acidified with concentrated hydrochloric acid and extracted with dichloromethane. The extract is dried (Na 2 SO4) and the solvent removed. The residue is crystallized from hexane to give 3-[3-trifluoromethylbenzoyl]propionic acid as crystals, mp. 80°-82° C.

후처리

  1. additionTo the mixture is added 10 ml
  2. customthe solvent removed under vacuum
  3. additionToluene is added several times
  4. customthe solvent removed
  5. stirringThe residue is stirred with ether
  6. filtrationfiltered
  7. customthe solvent evaporated

출처 및 근거

ORD 기록
ord-61b59cba0d30453cb1025ff577c22699
출처 데이터셋
uspto-grants-1980_10
특허 번호
US04226775

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