Reaction #49175

Reaction equation

Compound 17

2-(2-Hexadecyl-2,5,7,8-tetramethyl-chroman-6-yloxy)-ethanol

disuccinimidyl carbonate

triethylamine

acetonitrile

→

Compound 18

Yield 77.0%

Carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 2-(2-hexadecyl-2,5,7,8-tetramethyl-chroman-6-yloxy)-ethyl ester

Yield 77.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otherevaporated dryness
2. 2
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (300 mL)
3. 3
   WashIt was washed with saturated NaHCO3 aqueous solution (3×100 mL)
4. 4
   DryingThe organic layer was dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated to dryness

Procedure

Compound 17 (10.5 g, 22 mmol) was dissolved in anhydrous dichloromethane (150 mL). To the solution were added disuccinimidyl carbonate (8.45 g, 33 mmol), triethylamine (20 mL) and acetonitrile (50 mL). The reaction mixture was stirred at room temperature under argon for over night and then evaporated dryness. The residue was dissolved in dichloromethane (300 mL). It was washed with saturated NaHCO3 aqueous solution (3×100 mL). The organic layer was dried over Na2SO4, filtered and evaporated to dryness. Compound 18 (10.4 g, 77%) was obtained as colorless powder after drying in high vacuum, which was directly used for the next step without further purification.

Source