Reaction #985288

Reaction equation

2-{2-[2-(2-{2-[2-(11-mercapto-undecyloxy)-ethoxy]-ethoxyl}-ethoxy)-ethoxy]-ethoxy}-ethanol

triphenylmethyl chloride

→

4

Yield 49.2%

2-{2-[2-(2-{2-[2-(11-Tritylsulfanyl-undecyloxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethanol

Yield 49.2%

Solvents

THF

Conditions

Workup

1. 1
   Concentrationthe reaction mixture was concentrated
2. 2
   OtherThe crude residue was purified by flash chromatography (gradient elution, EtOAc to 20:1 EtOAc/MeOH)

Procedure

To a solution of 2-{2-[2-(2-{2-[2-(11-mercapto-undecyloxy)-ethoxy]-ethoxyl}-ethoxy)-ethoxy]-ethoxy}-ethanol (3) (1.22 g, 2.6 mmol) prepared according to the method of Pale-Grosdemange et al.†, dissolved in 10 mL of THF was added triphenylmethyl chloride (1.46 g, 5.2 mmol). After stirring at room temperature for 48 hours, the reaction mixture was concentrated. The crude residue was purified by flash chromatography (gradient elution, EtOAc to 20:1 EtOAc/MeOH) to afford 910 mg (49%) of 4. 1H NMR (CDCl3, 400 MHz) d 7.36 (d, J=X Hz, 6H), 7.22 (t, J=X Hz, 6H), 7.15 (t, J=X Hz, 3H), 3.72-3.48 (br m, 24H), 3.40 (t, J=X Hz, 2H), 2.08 (t, J=X Hz, 2H), 1.52 (m, 2H), 1.4-0.9 (br, 16H). ES-MS: m/z 733.4 (M+Na+). †Pale-Grosdemange, C.; Simon, E. S.; Prime, K. L.; Whitesides, G. M. J. Am. Chem. Soc, 1991, 113,12-20.

Source