4-Hydroxybenzaldehyde → 4-(3-(Diethylamino)propoxy)benzaldehyde

Temperature

90 °C

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.

1. additionwas added to the reaction mixture
2. temperatureAfter cooling to rt
3. customthe reaction was quenched by cold H2O (100 mL)
4. extractionthe resulting mixture was extracted with EtOAc (3×100 mL)
5. washThe combined EtOAc extracts were washed with brine (3×50 mL)
6. dry with materialdried (anhydrous Na2SO4)
7. customThe solvent was removed in vacuo
8. customthe crude product was purified by silica gel column chromatography (eluting with 10% MeOH in DCM+0.5% Et3N)

ORD record

ord-90d873b15330492480da5922dad1f4cf

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07361678B2