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 2075648Notes

Reaction equation

HRID 2075648 reaction equation
[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

Participants

6

Reactant 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

Product 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]-benzeneYield 118.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent3×

Procedure

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%).

Workup

  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))

Sources & evidence

ORD record
ord-07b2e74a918c4e51a44c8e0c466b6549
Source dataset
uspto-grants-2011_04
Patent number
US07919653B2

Reaction notes

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