Water → HCID 11329919, compound

HRID 1441889Notes

Reaction equation

HRID 1441889 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].[C:20](Cl)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>C(#N)C.N1C=CC=CC=1>[C:21]1([C:20]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[O:18][CH2:17][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])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 962WaterHCID 6456Trityl chlorideHCID 17472Hexaethylene Glycol

Product 1

HCID 11329919HCID 11329919, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6342AcetonitrileSolvent

Procedure

25 g of hexaethyleneglycol was dissolved in a mixture of 100 mL of acetonitrile and 30 mL of pyridine, to which 12.5 g of trityl chloride was added at 0° C., and then the solution was stirred overnight at room temperature. The reaction solution was mixed with iced water and subjected to extraction with ethyl acetate, and then the organic layer washed with water and concentrated under reduced pressure after drying. The residue was purified with silica gel column chromatography to obtain 15.7 g of the objective compound.

Workup

  1. additionwas added at 0° C.
  2. extractionsubjected to extraction with ethyl acetate
  3. washthe organic layer washed with water
  4. concentrationconcentrated under reduced pressure
  5. customafter drying
  6. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-c159b4431ed44a318c9d1699cff8ed21
Source dataset
uspto-grants-2010_02
Patent number
US07655768B2

Reaction notes

Loading…