تفاعل #45929

معادلة التفاعل

4-hydroxybenzaldehyde

Cs2CO3

mesylate

3-diethylamino-1-propanol

methanesulfonyl chloride

→

4-(3-diethylaminopropoxy)benzaldehyde

المذيبات

DMSO

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added to the reaction mixture
2. 2
   درجة الحرارةAfter cooling to rt
3. 3
   أخرىthe reaction was quenched by cold H2O (100 mL)
4. 4
   استخلاصthe resulting mixture was extracted with EtOAc (3×100 mL)
5. 5
   غسيلThe combined EtOAc extracts were washed with brine (3×50 mL)
6. 6
   تجفيفdried (anhydrous Na2SO4)
7. 7
   أخرىThe solvent was removed in vacuo
8. 8
   أخرىthe crude product was purified by silica gel column chromatography (eluting with 10% MeOH in DCM+0.5% Et3N)

الإجراء التجريبي

To a stirred solution of 4-hydroxybenzaldehyde (20 mmol) in DMSO (80 mL) at rt, solid Cs2CO3 (50 mmol) was added. The mesylate prepared from 3-diethylamino-1-propanol and methanesulfonyl chloride, General Procedure P2 (30 mmol) was added to the reaction mixture and heated to 90° C. until the reaction was complete. After cooling to rt, the reaction was quenched by cold H2O (100 mL), and the resulting mixture was extracted with EtOAc (3×100 mL). The combined EtOAc extracts were washed with brine (3×50 mL) and dried (anhydrous Na2SO4). The solvent was removed in vacuo, and the crude product was purified by silica gel column chromatography (eluting with 10% MeOH in DCM+0.5% Et3N) to afford 4-(3-diethylaminopropoxy)benzaldehyde.

المصدر