Dimethylformamide → Methyl 3-cyano-5-ethoxybenzoate

HRID 1096941ノート

反応式

HRID 1096941 の反応式
[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]

参加物

6

反応物 2

HCID 6228DimethylformamideHCID 57930910HCID 57930910、化合物

生成物 1

HCID 21942546Methyl 3-cyano-5-ethoxybenzoate

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-72a347b9fa904d5dad72e8110d081e2b
出典データセット
uspto-grants-2012_03
特許番号
US08138197B2

反応ノート

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