홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Cesium carbonate → Ethyl (3-{4-[(diphenylmethylene)amino]phenyl}cyclohexyl)acetate

HRID 1713846
노트
인쇄 미리보기

반응식

HRID 1713846 반응식
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][CH2:16][CH:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14]2)=[CH:9][CH:8]=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[C:79](=[NH:92])([C:86]1[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=1)[C:80]1[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:80]1([C:79](=[N:92][C:7]2[CH:12]=[CH:11][C:10]([CH:13]3[CH2:18][CH2:17][CH2:16][CH:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14]3)=[CH:9][CH:8]=2)[C:86]2[CH:87]=[CH:88][CH:89]=[CH:90][CH:91]=2)[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 59464250Ethyl [3-(4-{[(trifluoromethyl)sulphonyl]oxy}phenyl)cyclohexyl]acetate

생성물 1

HCID 59464258Ethyl (3-{4-[(diphenylmethylene)amino]phenyl}cyclohexyl)acetate수율 38%

시약·촉매·용매 2

HCID 167845
palladium(II) acetate
촉매
HCID 8028Tetrahydrofuran용매

실험 절차

Ethyl [3-(4-{[(trifluoromethyl)sulphonyl]oxy}phenyl)cyclohexyl]acetate (322 mg, 0.85 mmol) was stirred in dry THF (8 mL) under a nitrogen atmosphere and caesium carbonate (387 mg, 1.19 mmol), palladium(II) acetate (12 mg, 0.05 mmol) and BINAP (32 mg, 0.05 mmol) were added followed by benzophenone imine (0.214 mL, 1.27 mmol). The reaction vessel was degassed 6 times and stirred under reflux for 16 h. The mixture was extracted with ether (2×100 mL) and washed with water (100 mL). The organic extracts were dried and concentrated by evaporation to give an oil that was purified by chromatography eluting with 0-30% EtOAc/isohexane to give the title compound (137 mg, 38%) as an oil; 1H NMR δ 0.81-2.48 (m, 9H), 1.12-1.21 (m, 3H), 2.58-2.72 (m, 1H), 3.97-4.12 (m, 2H), 6.57-6.65 (m, 1H), 6.94-7.04 (m, 1H), 7.10-7.18 (m, 1H), 7.29-7.36 (m, 1H), 7.37-7.78 (m, 10H); MS m/e MH+ 426.

후처리

  1. customThe reaction vessel was degassed 6 times
  2. temperatureunder reflux for 16 h
  3. extractionThe mixture was extracted with ether (2×100 mL)
  4. washwashed with water (100 mL)
  5. customThe organic extracts were dried
  6. concentrationconcentrated by evaporation
  7. customto give an oil that
  8. customwas purified by chromatography
  9. washeluting with 0-30% EtOAc/isohexane

출처 및 근거

ORD 기록
ord-0a90d8daa0af45c696388dce9fddc3fe
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07795283B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트