Réaction #1470440

Équation de réaction

Water

propofol

2,6-diisopropylphenol

adipoyl chloride

→

2,6-diisopropylphenol hydrogen adipate

Rendement 40.0%

Solvants

methylene chloride

methylene chloride

Conditions de réaction

Traitement

1. 1
   Autreto reach room temperature
2. 2
   workup.STIRRINGthe two-phase mixture was stirred for 1 hr
3. 3
   LavageThe organic phase was washed with 3% aqueous HCl
4. 4
   Autredried
5. 5
   AutreSolvents were removed under vacuum
6. 6
   workup.ADDITIONThe fractions containing the ester
7. 7
   Autreevaporated under vacuum

Mode opératoire

Synthesis of propofol hemiadipate Triethylamine (6.26 ml, 45 mmol) and 4-dimethylaminopyridine (50 mg, 0.4 mmol) in methylene chloride (30 ml) were added to a solution of 2,6-diisopropylphenol (5.2 ml, 28 mmol) and adipoyl chloride (4.4 ml, 30 mmol) in methylene chloride (50) at 0° C. The mixture was allowed to reach room temperature and stirred at that temperature for 2 hr. Water (50 ml) was added, and the two-phase mixture was stirred for 1 hr. The organic phase was washed with 3% aqueous HCl and then dried. Solvents were removed under vacuum, and the oily residue was chromatogrammed on a silica gel column using chloroform-methanol (10:0.1) and then chloroform-methanol-acetic acid (10:0.1:0.01). The fractions containing the ester were pooled and evaporated under vacuum to yield 3.4 g (40% yield) of 2,6-diisopropylphenol hydrogen adipate (propofol hemiadipate) as an oil.

Source