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Sodium hydride → 1,3-Bis-[2-(2-{2-[2-(2-benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-5-[2-(2-{2-[2-(2-trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-benzene

HRID 2075648
ノート
印刷プレビュー

反応式

HRID 2075648 の反応式
[H-].[Na+].[C:3]([O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][C:38]1[CH:39]=[C:40]([OH:45])[CH:41]=[C:42]([OH:44])[CH:43]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:47][CH2:48][O:49][CH2:50][CH2:51][O:52][CH2:53][CH2:54][O:55][CH2:56][CH2:57][O:58][CH2:59][CH2:60][O:61][CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1>C1COCC1.CN(C=O)C>[CH2:62]([O:61][CH2:60][CH2:59][O:58][CH2:57][CH2:56][O:55][CH2:54][CH2:53][O:52][CH2:51][CH2:50][O:49][CH2:48][CH2:47][O:45][C:40]1[CH:39]=[C:38]([O:37][CH2:36][CH2:35][O:34][CH2:33][CH2:32][O:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][O:25][CH2:24][CH2:23][O:22][C:3]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:43]=[C:42]([O:44][CH2:36][CH2:35][O:34][CH2:33][CH2:32][O:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][O:25][CH2:24][CH2:23][O:22][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:41]=1)[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 5868775516-Bromo-1-phenyl-2,5,8,11,14-pentaoxahexadecaneHCID 670890515-[2-(2-{2-[2-(2-Trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-benzene-1,3-diol

生成物 1

HCID 866070451,3-Bis-[2-(2-{2-[2-(2-benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-5-[2-(2-{2-[2-(2-trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-benzene収率 118.7%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回
HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To an ice-cooled mixed suspension of sodium hydride (350 mg, 8.8 mmol; 60% in mineral oil) in THF (4.5 ml) and DMF (1.5 ml), a mixed solution of Compound 45 (1.0 g, 1.7 mmol) in THF (4.5 ml) and DMF (1.5 ml) was gradually added, and this was followed by stirring for 30 minutes. A solution of Compound 20 (2.7 g, 6.8 mmol) in THF (4 ml) was added thereto, and this was followed by stirring for 20 minutes. After the ice bath was removed, stirring was further conducted at room temperature for 4 hours. After the product was again immersed in the ice bath, water was carefully added to stop the reaction, and this was followed by concentration under reduced pressure. Extraction from ethyl acetate was conducted, and the combined organic phases were washed with saturated brine and dried with anhydrous sodium sulfate. Filtration and concentration under reduced pressure were conducted, after which the residue obtained was purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (ethyl acetate-ethyl acetate:methanol 19:1)) to yield Compound 46 (light-yellow oil 1.22 g, 59%).

後処理

  1. additionmixed
  2. stirringby stirring for 20 minutes
  3. customAfter the ice bath was removed
  4. stirringstirring
  5. waitwas further conducted at room temperature for 4 hours
  6. additionwas carefully added
  7. customthe reaction
  8. concentrationthis was followed by concentration under reduced pressure
  9. extractionExtraction from ethyl acetate
  10. washthe combined organic phases were washed with saturated brine
  11. dry with materialdried with anhydrous sodium sulfate
  12. filtrationFiltration and concentration under reduced pressure
  13. customafter which the residue obtained
  14. customwas purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (ethyl acetate-ethyl acetate:methanol 19:1))

出典と根拠

ORDレコード
ord-07b2e74a918c4e51a44c8e0c466b6549
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

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