Pyridine → HCID 23508700, compound

HRID 1883942Notes

Reaction equation

HRID 1883942 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[CH3:12][O:13][C:14]1[CH:35]=[CH:34][C:17]([C:18](Cl)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:16][CH:15]=1.[N:36]1[CH:41]=[CH:40]C=[CH:38][CH:37]=1>>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([C:18]([O:1][CH2:2][C:3]2[CH:4]=[CH:5][C:6]([C:7]([O-:9])=[O:8])=[CH:10][CH:11]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:17]2[CH:34]=[CH:35][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)=[CH:24][CH:23]=1.[CH2:37]([NH+:36]([CH2:11][CH3:3])[CH2:41][CH3:40])[CH3:38]

Participants

4

Reactant 3

HCID 1049PyridineHCID 763604-(Hydroxymethyl)benzoic acidHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)

Product 1

HCID 23508700HCID 23508700, compound

Procedure

A solution of commercial 4-(hydroxymethyl)benzoic acid (1.52 g, 10.0 mmol) in pyridine (50 mL) is treated with 4,4′-dimethoxytrityl chloride (3.73 g, 11.0 mmol) overnight at room temperature and concentrated to an oil in vacuo. The residue is dissolved in a mixture of MeOH and CH2Cl2 (95:5, v/v; 200 mL) and washed with 2 M aqueous triethylammonium acetate (5×20 mL). The organic solution is evaporated, re-dissolved in CH2Cl2, dried over Na2SO4, and evaporated to give crude triethylammonium 4-[[(4,4′-dimethoxytrityl)oxy]methyl]-benzoate in quantitative yield (1016 mg).

Workup

  1. concentrationconcentrated to an oil in vacuo
  2. dissolutionThe residue is dissolved in a mixture of MeOH and CH2Cl2 (95:5
  3. wash200 mL) and washed with 2 M aqueous triethylammonium acetate (5×20 mL)
  4. customThe organic solution is evaporated
  5. dissolutionre-dissolved in CH2Cl2
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-7e794dbb1b204d3f85f63cefe75aa15d
Source dataset
uspto-grants-2004_07
Patent number
US06762281B2

Reaction notes

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