Sodium Carbonate → HCID 54035333, 화합물

HRID 1588088노트

반응식

HRID 1588088 반응식
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]

참가 물질

9

반응물 4

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

생성물 1

HCID 54035333HCID 54035333, 화합물수율 54.1%

시약·촉매·용매 4

HCID 11776Triphenylphosphine촉매HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ab65fbff37874b288c7d8c6268de9458
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05220050

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