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N,N,N',N'-Tetramethylazodicarboxamide → 1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-5-[2-(2-{2-[2-(2-trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-benzene

HRID 2075646
ノート
印刷プレビュー

反応式

HRID 2075646 の反応式
[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.[C:49]([Si:53]([CH3:71])([CH3:70])[O:54][C:55]1[CH:56]=[C:57](O)[CH:58]=[C:59]([O:61][Si:62]([C:65]([CH3:68])([CH3:67])[CH3:66])([CH3:64])[CH3:63])[CH:60]=1)([CH3:52])([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:65]([Si:62]([CH3:64])([CH3:63])[O:61][C:59]1[CH:58]=[C:57]([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:56]=[C:55]([O:54][Si:53]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:71])[CH3:70])[CH:60]=1)([CH3:68])([CH3:67])[CH3:66]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 230808033,5-Bis-(tert-butyl-dimethyl-silanyloxy)-phenolHCID 54298879Tr-PEG6

生成物 1

HCID 670892321,3-Bis-(tert-butyl-dimethyl-silanyloxy)-5-[2-(2-{2-[2-(2-trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-benzene収率 39%

試薬・触媒・溶媒

2
HCID 1140Toluene溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of Compound 2 (4.3 g, 8.9 mmol) in toluene (20 ml), tributylphosphine (2.35 g, 8.92 mmol) was added at room temperature; this was followed by stirring for 1 hour. This was gradually added to a solution of Compound 43 (3.3 g, 11.6 mmol) and 1,1′-azobis(N,N-dimethylformamide) (2.0 g, 11.6 mmol) in toluene (20 ml), and this was followed by overnight stirring at room temperature. Ethyl acetate (100 ml) was added; the resulting insoluble matter was removed by Celite filtration and washed 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 3:1-2:1)) to yield Compound 44 (colorless oil 2.8 g, 39%).

後処理

  1. waitthis was followed by overnight
  2. stirringstirring at room temperature
  3. customthe resulting insoluble matter was removed by Celite filtration
  4. washwashed with ethyl acetate
  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 3:1-2:1))

出典と根拠

ORDレコード
ord-95dccbf0e6964569b851efd3dd9e4603
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07919653B2

反応ノート

読み込み中…

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