Hexaethylene Glycol → HCID 70167335, compound

HRID 1699795Notes

Reaction equation

HRID 1699795 reaction equation
[CH2:1]([OH:19])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18].[CH3:20][O:21][C:22]1([O:42][CH3:43])[CH:41]=[CH:40][C:25]([C:26](Cl)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:24][CH2:23]1>N1C=CC=CC=1>[CH3:43][O:42][C:22]1([O:21][CH3:20])[CH:23]=[CH:24][C:25]([C:26]([CH:17]([OH:18])[CH2:16][O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][OH:19])([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:40][CH2:41]1

Participants

4

Reactant 2

HCID 17472Hexaethylene GlycolHCID 534461344,4-Dimethoxytrityl chloride

Product 1

HCID 70167335HCID 70167335, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of hexaethylene glycol (8.46 grams, 30 mmoles) in 250 ml dry pyridine, a solution of 4,4-dimethoxytrityl chloride (3.38 grams, 10 mmoles) in 50 ml dry pyridine was added dropwise at room temperature. The resulting solution was stirred at room temperature for additional 5 hours. The solvent was then evaporated to dryness, and the residue was extracted with 200 ml ethylacetate/200 ml 5% sodium bicarbonate solution, washed twice with water and twice with brine solution. The obtained organic layer was dried over anhydrous sodium sulfate, evaporated and purified by silica gel column chromatography using 5% methanol in dichloromethane, 0.5% pyridine. The resulting 4,4-dimethoxytrityl-hexaethylene glycol compound (5.23 grams, 89% yield) migrated with Rf=0.29.

Workup

  1. customThe solvent was then evaporated to dryness
  2. extractionthe residue was extracted with 200 ml ethylacetate/200 ml 5% sodium bicarbonate solution
  3. washwashed twice with water and twice with brine solution
  4. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  5. customevaporated
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-e33c8278c1764fa4ad199b7762139471
Source dataset
uspto-grants-2002_02
Patent number
US06348583B1

Reaction notes

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