Pyridine → HCID 22633851, compound

HRID 1369312Notes

Reaction equation

HRID 1369312 reaction equation
[CH2:1]([OH:13])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12].N1C=CC=CC=1.[CH3:20][O:21][C:22]1[CH:43]=[CH:42][C:25]([C:26](Cl)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)=[CH:24][CH:23]=1>O1CCOCC1>[CH3:34][O:33][C:30]1[CH:29]=[CH:28][C:27]([C:26]([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:13])([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:25]2[CH:42]=[CH:43][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 8200Tetraethylene GlycolHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)

Product 1

HCID 22633851HCID 22633851, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Tetraethyleneglycol (14.0 g, 72 mmol) was coevaporated with dry pyridine (2×50 mL), dissolved in dry dioxane and 4,4′-dimethoxytrityl chloride (8.0 g, 23.6 mmol) was added portion-wise to the stirred solution. The reaction was monitored by TLC. After overnight stirring at ambient temperature, the reaction mixture was evaporated and dissolved in CH2Cl2 (200 mL), and washed with saturated aq. NaHCO3 (3×100 mL) and brine (100 mL). The organic phase was dried over Na2SO4 and concentrated. Purification on silica gel column using a stepwise gradient of MeOH (0 to 10%) in H2Cm2 containing 0.2% pyridine yielded 8.5 g (73%) of the title compound.

Workup

  1. customthe reaction mixture was evaporated
  2. dissolutiondissolved in CH2Cl2 (200 mL)
  3. washwashed with saturated aq. NaHCO3 (3×100 mL) and brine (100 mL)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated
  6. customPurification on silica gel column

Sources & evidence

ORD record
ord-3e77ddf6d53844b183b8319965163777
Source dataset
uspto-grants-2003_06
Patent number
US06576752B1

Reaction notes

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