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Sodium Carbonate → HCID 69546259, 화합물

HRID 1744680
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HRID 1744680 반응식
FC(F)(F)S(O[C:7]1[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][CH2:9][C:8]=1[C:20](OCC)=O)(=O)=O.[Cl:27][C:28]1[CH:33]=[CH:32]C(B(O)O)=[CH:30][CH:29]=1.[C:37](=[O:40])([O-])[O-:38].[Na+].[Na+].[C:43]1(C)C=CC=C[CH:44]=1.C(O)C>C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:27][C:28]1[CH:29]=[CH:30][C:20]([C:8]2[CH2:9][CH2:10][N:11]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:12][C:7]=2[C:37]([O:38][CH2:43][CH3:44])=[O:40])=[CH:32][CH:33]=1
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참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 21863594Toluene ethanolHCID 22228415455954-80-0

생성물 1

HCID 69546259HCID 69546259, 화합물

시약·촉매·용매 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

A vigorously stirred suspension of the product of step C (1.00 g, 2.48 mmol), 4-chlorophenylboronic acid (0.427 g, 2.73 mmol) and [1,1′-bis(diphenylphosphino)-ferrocene)dichloropalladium(II) (0.102 g, 0.124 mmol) in toluene/ethanol (3:2; 24.0 mL) was degassed via three vacuum/nitrogen ingress cycles and then heated to approximately 80° C. Aqueous 2 M sodium carbonate (3.10 mL, 6.20 mmol) was added dropwise via syringe and the resulting mixture maintained at reflux overnight. After cooling to ambient temperature, the reaction mixture was diluted with ethyl acetate and filtered through celite®. The filtrate was poured into water and extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification of the residue by medium pressure liquid chromatography on silica gel (gradient elution; 0–15% ethyl acetate/hexanes as eluent) furnished the title compound as a colorless oil (0.828 g).

후처리

  1. customwas degassed via three vacuum/nitrogen ingress cycles
  2. temperaturethe resulting mixture maintained
  3. temperatureat reflux overnight
  4. temperatureAfter cooling to ambient temperature
  5. filtrationfiltered through celite®
  6. additionThe filtrate was poured into water
  7. extractionextracted three times with ethyl acetate
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo
  11. customPurification of the residue by medium pressure liquid chromatography on silica gel (gradient elution; 0–15% ethyl acetate/hexanes as eluent)

출처 및 근거

ORD 기록
ord-c528eac3e5104205a8f4c2533514739f
출처 데이터셋
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07015235B2

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