Pyridine → HCID 22633851, compound

HRID 2417288Notes

Reaction equation

HRID 2417288 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 CH2Cl2 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-e906dce9f0774a96adf0cdb418d1755f
Source dataset
uspto-grants-2004_11
Patent number
US06825331B2

Reaction notes

Loading…