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Dimethylformamide → Ethyl 2-(4-cyano-3-methoxyphenyl)propanoate

HRID 1428752
ノート
印刷プレビュー

反応式

HRID 1428752 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[O:15][CH3:16].[CH3:17][N:18](C)C=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:17]([C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[O:15][CH3:16])#[N:18]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 6228DimethylformamideHCID 70855859Ethyl 2-(4-iodo-3-methoxyphenyl)propanoate

生成物 1

HCID 66643920Ethyl 2-(4-cyano-3-methoxyphenyl)propanoate収率 51%

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 11979704Tetrakis(triphenylphosphine)palladium触媒
HCID 8857
Ethyl Acetate
溶媒

反応条件

温度
120 °C

実験手順

To a stirred solution of ethyl 2-(4-iodo-3-methoxyphenyl)propanoate (626 mg, 1.873 mmol) in dimethylformamide were added zinc cyanide (227 mg, 1.929 mmol) and tetrakis(triphenylphosphine) palladium (216 mg, 0.1873 mmol). The reaction mixture was stirred for 36 h at 120° C., then cooled to room temperature, diluted with ethyl acetate. The mixture was filtered using celite pad. The filtrate dissolved in ethyl acetate and extracted with NaHCO3. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. Ethyl 2-(4-cyano-3-methoxyphenyl)propanoate (222 mg) was obtained as 51% yield.

後処理

  1. temperaturecooled to room temperature
  2. filtrationThe mixture was filtered
  3. dissolutionThe filtrate dissolved in ethyl acetate
  4. extractionextracted with NaHCO3
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate removed in vacuo
  8. customThe crude was purified by column chromatography

出典と根拠

ORDレコード
ord-0453661a1b554bf29fb5f9f05c19e92a
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08937092B2

反応ノート

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