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Sodium hydride → [2-(2-{2-[2-(2-{3,5-Bis-[2-(2-{2-[2-(2-benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-acetic acid tert-butyl ester

HRID 2075650
ノート
印刷プレビュー

反応式

HRID 2075650 の反応式
[H-].[Na+].[CH2:3]([O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][C:26]1[CH:27]=[C:28]([CH:45]=[C:46]([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][CH2:62][O:63][CH2:64][C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[CH:47]=1)[O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][OH:44])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:71]([O:75][C:76](=[O:79])[CH2:77]Br)([CH3:74])([CH3:73])[CH3:72]>C1COCC1.CN(C=O)C.C1COCC1>[C:71]([O:75][C:76](=[O:79])[CH2:77][O:44][CH2:43][CH2:42][O:41][CH2:40][CH2:39][O:38][CH2:37][CH2:36][O:35][CH2:34][CH2:33][O:32][CH2:31][CH2:30][O:29][C:28]1[CH:27]=[C:26]([O:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH2:12][CH2:11][O:10][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:47]=[C:46]([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][CH2:62][O:63][CH2:64][C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[CH:45]=1)([CH3:74])([CH3:73])[CH3:72]
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 79177tert-Butyl bromoacetateHCID 586877452-(2-{2-[2-(2-{3,5-Bis-[2-(2-{2-[2-(2-benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethanol

生成物 1

HCID 86607046[2-(2-{2-[2-(2-{3,5-Bis-[2-(2-{2-[2-(2-benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-acetic acid tert-butyl ester収率 45%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 21974620tetrahydrofuran N,N-dimethylformamide溶媒

実験手順

To an ice-cooled suspension of sodium hydride (175 mg, 4.4 mmol; 60% in mineral oil) in THF/DMF (4/1 mixed fluid 5 ml), a solution of Compound 47 (1.05 g, 1.09 mmol) in THF (5 ml) was gradually added, and this was followed by stirring for 30 minutes. A solution of bromoacetic acid tert-butyl ester (847 mg, 4.3 mmol) in THF (6 ml) was added thereto. 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 extraction from ethyl acetate, 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 solution containing 5% methanol)) to yield Compound 48 (light-yellow oil 530 mg, 45%).

後処理

  1. customAfter the ice bath was removed
  2. stirringstirring
  3. waitwas further conducted at room temperature for 2 hours
  4. additionWater was carefully added
  5. customthe reaction
  6. extractionthis was followed by extraction from ethyl acetate
  7. washthe combined organic phases were washed with saturated brine
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationFiltration and concentration under reduced pressure
  10. customafter which the residue obtained
  11. customwas purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (ethyl acetate-ethyl acetate solution containing 5% methanol))

出典と根拠

ORDレコード
ord-f4c1185b2c8144989018ab4be32b6635
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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