Sodium Carbonate → HCID 54035333、化合物

HRID 1588088ノート

反応式

HRID 1588088 の反応式
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C([O-])(=O)C.[K+].[C:15]([OH:21])(=[O:20])[CH2:16][CH2:17][CH:18]=[CH2:19].C(=O)([O-])[O-].[Na+].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C=O)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([CH:19]=[CH:18][CH2:17][CH2:16][C:15]([OH:21])=[O:20])=[CH:3][CH:4]=1)#[N:7]

参加物

9

反応物 4

HCID 10340Sodium CarbonateHCID 12162Benzonitrile, 4-bromo-HCID 611384-Pentenoic acidHCID 517044Potassium Acetate

生成物 1

HCID 54035333HCID 54035333、化合物収率 54.1%

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒2 回

実験手順

Tetrabutylammonium chloride (hydrate, 17.8 g) was dried by azeotroping with benzene (250 mL round bottom flask equipped with a Dean-Stark apparatus). The benzene was removed in vacuo affording anhydrous tetrabutylammonium chloride (17.0 g, 61.2 mmol). To this flask under argon were added triphenylphosphine (820 mg, 3.13 mmol), palladium acetate (703 mg, 3.13 mmol), 4-bromobenzonitrile (16.9 g, 92.8 mmol), potassium acetate (36.8g, 375 mmol) and 100 mL of degassed anhydrous dimethylformamide (degassed by bubbling argon through for 10 min, dried over molecular sieves). A solution of 4-pentenoic acid (6.27 g, 62.6 mmol) and degassed anhydrous DMF (35 mL) was then added to the rapidly stirring reaction mixture at 23° C. After 21 hours at 23° C, the reaction mixture was poured slowly into a sodium carbonate solution (3%, 400 mL) and extracted with ethyl acetate (500 mL). The aqueous layer was treated with decolorizing carbon, and filtered. Then, the aqueous layer was acidified to a pH of 2 with 10% HCl which afforded the title compound as a white solid (6.82 g, 54%): m.p. 150°-167° C.

後処理

  1. dry with materialTetrabutylammonium chloride (hydrate, 17.8 g) was dried
  2. customby azeotroping with benzene (250 mL round bottom flask
  3. customequipped with a Dean-Stark apparatus)
  4. customThe benzene was removed in vacuo
  5. additionwas then added to the
  6. customreaction mixture at 23° C
  7. extractionextracted with ethyl acetate (500 mL)
  8. additionThe aqueous layer was treated with decolorizing carbon
  9. filtrationfiltered

出典と根拠

ORDレコード
ord-ab65fbff37874b288c7d8c6268de9458
出典データセット
uspto-grants-1993_06
特許番号
US05220050

反応ノート

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