Tetraethylene Glycol → 1-Phenyl-2,5,8,11,14,17,20,23-octaoxapentacosan-25-ol

HRID 6627

반응식

HRID 6627 반응식
[H-].[Na+].[CH2:3]([OH:15])[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13]O.S([O-])(=O)(=O)C.[CH2:21]([O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][OH:40])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1>[CH2:21]([O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][OH:15])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

참가 물질

6

반응물 4

HCID 8200Tetraethylene GlycolHCID 24758Sodium hydrideHCID 85257MethanesulfonateHCID 110769571-Phenyl-2,5,8,11-tetraoxatridecan-13-ol

생성물 1

HCID 574377031-Phenyl-2,5,8,11,14,17,20,23-octaoxapentacosan-25-ol수율 34.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a solution of tetrahydrofuran (140 mL) containing sodium hydride (0.43 g, 18 mmol) was added dropwise a solution of non-polydispersed tetraethylene glycol (3.5 g, 18 mmol) in tetrahydrofuran (10 mL) and the reaction mixture was stirred for 1 h. Then mesylate of non-polydispersed tetraethylene glycol monobenzylether 40 (6.0 g, 16.5 mmol) dissolved in tetrahydrofuran (10 mL) was added dropwise and the reaction mixture was stirred overnight. The crude reaction mixture was filtered through Celite (washed, CH2Cl2, 250 mL) and the filtrate was washed H2O, dried MgSO4, and evaporated to dryness. The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) and chromatographed (silica, chloroform/methanol, 25:1) to afford the non-polydispersed title compound as a clear oil (2.62 g, 34% yield).

후처리

  1. additionwas added dropwise
  2. stirringthe reaction mixture was stirred overnight
  3. customThe crude reaction mixture
  4. filtrationwas filtered through Celite (washed, CH2Cl2, 250 mL)
  5. washthe filtrate was washed H2O, dried MgSO4
  6. customevaporated to dryness
  7. customThe resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1)
  8. customchromatographed (silica, chloroform/methanol, 25:1)

출처 및 근거

ORD 기록
ord-b2cbf350d667459bb6ec706b7b02f558
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084114B2

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