Water → Tr-PEG6

HRID 1441887Notes

Reaction equation

HRID 1441887 reaction equation
[CH2:1]([OH:16])[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][OH:15].[C:17](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>C(#N)C.N1C=CC=CC=1>[C:18]1([C:17]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[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:16])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 962WaterHCID 6456Trityl chlorideHCID 62551Pentaethylene glycol

Product 1

HCID 54298879Tr-PEG6Yield 31.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6342AcetonitrileSolvent

Procedure

10 g of pentaethyleneglycol was dissolved in a mixture of 100 mL of acetonitrile and 30 mL of pyridine, to which 11 g of trityl chloride were 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 6 g of the objective compound.

Workup

  1. additionwere 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-88180cfc0f6d48c79fdc1321a4aaaf14
Source dataset
uspto-grants-2010_02
Patent number
US07655768B2

Reaction notes

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