Dimethylformamide → 1-[2-(5-Nitro-2-pentafluoroethylphenoxy)-ethyl]-pyrrolidine

HRID 888079노트

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HRID 888079 반응식
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])=[C:8]([OH:10])[CH:9]=1)([O-:3])=[O:2].Cl.Cl[CH2:20][CH2:21][N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:11]([F:16])([F:17])[C:12]([F:13])([F:14])[F:15])=[C:8]([CH:9]=1)[O:10][CH2:20][CH2:21][N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)([O-:3])=[O:2]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 17756181Phenol, 5-nitro-2-(1,1,2,2,2-pentafluoroethyl)-

생성물 1

HCID 865946891-[2-(5-Nitro-2-pentafluoroethylphenoxy)-ethyl]-pyrrolidine

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

A flask was charged with 5-nitro-2-pentafluoroethylphenol (3.67 g, 14.2 mmol), 1-(2-chloroethyl)pyrrolidine hydrochloride (9.71 g, 57.1 mmol), DMF (20 mL) and combined with K2CO3 (5.9 g, 42.1 mmol) and heated to 70° C. for 24 h. The reaction was cooled to RT, taken up in to EtOAc and washed with 2N NaOH, and brine. The organic layer was dried with MgSO4, filtered and concentrated in vacuo. The aqueous layer was acidified, extracted with EtOAc and dried with MgSO4, filtered, concentrated in vacuo and combined with the other portion. The title compound was purified by column chromatography using 0-10% MeOH in CH2Cl2.

후처리

  1. temperatureThe reaction was cooled to RT
  2. washwashed with 2N NaOH, and brine
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. extractionextracted with EtOAc
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe title compound was purified by column chromatography

출처 및 근거

ORD 기록
ord-74d96a00683d4c3086922e478de404f8
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247556B2

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