N,N,N',N'-Tetramethylazodicarboxamide → Tert-butyl-dimethyl-{4-[2-(2-{2-[2-(2-trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}silane

HRID 2075631노트

반응식

HRID 2075631 반응식
[C:1]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][OH:35])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(P(CCCC)CCCC)CCC.[Si:49]([O:56][C:57]1[CH:62]=[CH:61][C:60](O)=[CH:59][CH:58]=1)([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50].N(C(N(C)C)=O)=NC(N(C)C)=O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:52]([Si:49]([CH3:51])([CH3:50])[O:56][C:57]1[CH:62]=[CH:61][C:60]([O:35][CH2:34][CH2:33][O:32][CH2:31][CH2:30][O:29][CH2:28][CH2:27][O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:59][CH:58]=1)([CH3:55])([CH3:54])[CH3:53]

참가 물질

7

반응물 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 5973884-(tert-Butyldimethylsiloxy)phenolHCID 54298879Tr-PEG6

생성물 1

HCID 23080801Tert-butyl-dimethyl-{4-[2-(2-{2-[2-(2-trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}silane수율 60.3%

시약·촉매·용매 2

HCID 1140Toluene용매3회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of Compound 2 (2.8 g, 5.8 mmol) in toluene (10 ml), a solution of tributylphosphine (1.17 g, 5.8 mmol) in toluene (2 ml) was added at room temperature; this was followed by stirring for 1 hour. This was gradually added to a solution of Compound 18 (1.1 g, 4.9 mmol) and 1,1′-azobis(N,N-dimethylformamide) (1.0 g, 5.8 mmol) in toluene (10 ml), and this was followed by overnight stirring at room temperature. Ethyl acetate was added; the resulting insoluble matter was removed by Celite filtration, and washing was conducted with ethyl acetate. The combined organic phases were concentrated under reduced pressure; the residue obtained was purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (n-hexane:ethyl acetate 2:1)) to yield Compound 21 (colorless oil 2.03 g, 60%).

후처리

  1. waitthis was followed by overnight
  2. stirringstirring at room temperature
  3. customthe resulting insoluble matter was removed by Celite filtration
  4. washwashing
  5. concentrationThe combined organic phases were concentrated under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (n-hexane:ethyl acetate 2:1))

출처 및 근거

ORD 기록
ord-156eef2c73ff44e1ba6cf4d2404bf72f
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919653B2

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