تفاعل #45964

معادلة التفاعل

mesylate

N,N-diethyaminopropanol

methanesulfonyl chloride

4′-hydroxyacetophenone

potassium carbonate

→

1-{4-[3-(diethylamino)propoxy]phenyl}ethanone

المردود 50.0%

المذيبات

water

EtOAc

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added to the reaction mixture
2. 2
   درجة الحرارةAfter cooling to rt
3. 3
   غسيلThe combined organic layers were washed with saturated sodium bicarbonate (2×15 ml), water (2×15 ml) and brine (15 ml)
4. 4
   تجفيفThe organic layer was dried over magnesium sulfate
5. 5
   أخرىthe solvent was removed in vacuuo

الإجراء التجريبي

To a stirred solution of 4′-hydroxyacetophenone (2.2 mmol) in DMF (10 mL) at rt, solid potassium carbonate (8.0 mmol) was added. The mesylate of N,N-diethyaminopropanol (prepared from the corresponding alcohol and methanesulfonyl chloride) (2.0 mmol) was added to the reaction mixture and heated to 80° C. until completion according to General Procedure Q1, as indicated by TLC or HPLC. After cooling to rt, the reaction mixture was diluted with water and the product was isolated in EtOAc. The combined organic layers were washed with saturated sodium bicarbonate (2×15 ml), water (2×15 ml) and brine (15 ml). The organic layer was dried over magnesium sulfate, and the solvent was removed in vacuuo to afford the desired 1-{4-[3-(diethylamino)propoxy]phenyl}ethanone. The crude alkylated product was purified using silica gel column chromatography. Pure product was obtained with 2-3% MeOH/DCM. (yield 50-60%)

المصدر