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 2075633Notes

Reaction equation

HRID 2075633 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: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

Participants

5

Reactant 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

Product 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]benzeneYield 84.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

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%).

Workup

  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))

Sources & evidence

ORD record
ord-ac00015991a440748bddc55cdb570735
Source dataset
uspto-grants-2011_04
Patent number
US07919653B2

Reaction notes

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