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Tert-butyl-dimethyl-(4-tributylstannanyl-but-3-enyloxy)-silane → 4'-[4-(Tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-biphenyl-4-carbonitrile

HRID 515060
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HRID 515060 반응식
[C:1]([Si:5]([CH3:25])([CH3:24])[O:6][CH2:7][CH2:8][CH:9]=[CH:10][Sn](CCCC)(CCCC)CCCC)([CH3:4])([CH3:3])[CH3:2].OS(C(F)(F)F)(=O)=O.[C:34]([C:36]1[CH:41]=[CH:40][C:39]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:38][CH:37]=1)#[N:35]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([Si:5]([CH3:24])([CH3:25])[O:6][CH2:7][CH2:8][CH:9]=[CH:10][C:45]1[CH:44]=[CH:43][C:42]([C:39]2[CH:38]=[CH:37][C:36]([C:34]#[N:35])=[CH:41][CH:40]=2)=[CH:47][CH:46]=1)([CH3:2])([CH3:3])[CH3:4]
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참가 물질

5

반응물 2

HCID 85142049Tert-butyl-dimethyl-(4-tributylstannanyl-but-3-enyloxy)-silaneHCID 874412284'-Cyanobiphenyl triflate

생성물 1

HCID 684069964'-[4-(Tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-biphenyl-4-carbonitrile

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

A solution of Example 31B (4.95 g, 10.4 mmol), 4′-cyanobiphenyl triflate (3.1 g, 9.48 mmol, prepared from 4′-hydroxybiphenyl-4-carbonitrile by standard methods), and Pd(PPh3)2Cl2 (0.332 g, 0.47 mmol) in DMF (20 mL) was stirred at 80° C. overnight. The mixture was cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (97.5:2.5 hexane/ethyl acetate) to provide the title compound. 1H NMR (300 MHz, CDCl3): δ 0.07 (s, 6H), 0.91 (s, 9H), 2.46 (q, J=6 Hz, 2H), 3.75 (t, J=6 Hz, 2H), 6.32 (d, J=16 Hz, 1H), 6.48 (d, J=16 Hz, 1H), 7.44 (d, J=9 Hz, 2H), 7.54 (d, J=9 Hz, 2H), 7.65-7.74 (m, 4H). MS (DCl—NH3) m/z 364 (M+H)+, m/z 359 (M+NH4)+.

후처리

  1. custompartitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by column chromatography (97.5:2.5 hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-96c09bc4bccd473f8dd9f42fe8f88eb8
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09108948B2

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