Dimethylformamide → Methyl 3-cyano-5-ethoxybenzoate

HRID 1096941노트

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HRID 1096941 반응식
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:11]=[C:12](OS(C(F)(F)F)(=O)=O)[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])[CH3:2].[CH3:22][N:23](C=O)C>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:22]([C:12]1[CH:11]=[C:6]([CH:5]=[C:4]([O:3][CH2:1][CH3:2])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])#[N:23]

참가 물질

6

반응물 2

HCID 6228DimethylformamideHCID 57930910HCID 57930910, 화합물

생성물 1

HCID 21942546Methyl 3-cyano-5-ethoxybenzoate

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

A mixture of methyl 3-ethoxy-5-trifluoromethanesulfonyloxybenzoate (308 mg, 0.94 mmol), zinc cyanide (165 mg, 1.41 mmol), tetrakis(triphenylphosphine)palladium(0) (54 mg, 0.05 mmol) and DMF (2.0 mL) was stirred in a nitrogen atmosphere at 80° C. for 12 hours. After left cooled, the reaction mixture was diluted with ethyl acetate (30 mL), washed with aqueous 14% ammonia and aqueous saturated sodium chloride solution, dried with sodium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography to obtain the title compound as a colorless solid.

후처리

  1. waitAfter left
  2. temperaturecooled
  3. washwashed with aqueous 14% ammonia and aqueous saturated sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified through silica gel column chromatography

출처 및 근거

ORD 기록
ord-72a347b9fa904d5dad72e8110d081e2b
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138197B2

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