Sodium hydride → 1-[2-(2-{2-[2-(2-Benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-4-[2-(2-{2-[2-(2-trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]benzene

HRID 2075633ノート

反応式

HRID 2075633 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:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=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[CH2:46][CH2:47][O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH2:55][CH2:56][O:57][CH2:58][CH2:59][O:60][CH2:61][C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1>C1COCC1>[CH2:61]([O:60][CH2:59][CH2:58][O:57][CH2:56][CH2:55][O:54][CH2:53][CH2:52][O:51][CH2:50][CH2:49][O:48][CH2:47][CH2:46][O:44][C:41]1[CH:42]=[CH:43][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:21]=[CH:20][CH:19]=[CH:18][CH:17]=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:39][CH:40]=1)[C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 5868775516-Bromo-1-phenyl-2,5,8,11,14-pentaoxahexadecaneHCID 670893454-[2-(2-{2-[2-(2-Trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]phenol

生成物 1

HCID 670892521-[2-(2-{2-[2-(2-Benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-4-[2-(2-{2-[2-(2-trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]benzene収率 84.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To an ice-cooled suspension of sodium hydride (800 mg, 20 mmol; 60% in mineral oil) in THF (15 ml), a solution of Compound 22 (1.2 g, 2.1 mmol) in THF (20 ml) was gradually added; this was followed by stirring for 20 minutes. A solution of Compound 20 (1.7 g, 4.3 mmol) in THF (12 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 2 hours. Water was carefully added to stop the reaction, and this was followed by concentration under reduced pressure. Extraction from methylene chloride was conducted, and the combined organic phases were washed with saturated brine and dried with anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the residue obtained was purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (n-hexane:ethyl acetate 2:1-1:1)) to yield Compound 23 (light-yellow oil 1.56 g, 84%).

後処理

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

出典と根拠

ORDレコード
ord-ac00015991a440748bddc55cdb570735
出典データセット
uspto-grants-2011_04
特許番号
US07919653B2

反応ノート

読み込み中…