Pyridine → 4-[(4,4'-Dimethoxytrityl)oxy]Butyric Acid, Triethylammonium Salt

Reaction equation

[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([C:7](Cl)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[OH:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30].[N:32]1[CH:37]=[CH:36]C=[CH:34][CH:33]=1>>[CH2:33]([NH+:32]([CH2:24][CH3:3])[CH2:37][CH3:36])[CH3:34].[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([C:7]([O:25][CH2:26][CH2:27][CH2:28][C:29]([O-:31])=[O:30])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

Reactant 3

HCID 1049Pyridine

HCID 104134-Hydroxybutyric Acid

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)

Product 1

HCID 235087064-[(4,4'-Dimethoxytrityl)oxy]Butyric Acid, Triethylammonium Salt

Procedure

A solution of 4,4′-dimethoxytrityl chloride (695 mg, 2.05 mmol) and 4-hydroxybutyric acid (208 mg, 2.0 mmol) in anhydrous Pyridine (20 mL) was stirred overnight and concentrated to an oil in vacuo. The residue was dissolved in a mixture of MeOH and CH2Cl2 (95:5, v/v; 200 mL) and washed with 2M aqueous triethylammonium acetate (5×20 mL). The organic solution was evaporated, re-dissolved in CH2Cl2, dried over Na2SO4, and evaporated to give the crude title compound in a quantitative yield (1016 mg).