Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].S([O-])(=O)(=O)C.[CH2:22]([N:24]([CH2:29][CH3:30])[CH2:25][CH2:26][CH2:27]O)[CH3:23].CS(Cl)(=O)=O>CN(C=O)C>[CH2:22]([N:24]([CH2:29][CH3:30])[CH2:25][CH2:26][CH2:27][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1)[CH3:23]Participants
Conditions
- Temperature
- 80 °C
Procedure
To a stirred solution of 4′-hydroxyacetophenone (91 mmol) in DMF (80 mL) at rt, solid potassium carbonate (153 mmol) was added. The mesylate prepared from 3-diethylamino-1-propanol and methanesulfonyl chloride (76 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 quenched by treating the mixture with saturated sodium bicarbonate. The aqueous layer was poured into EtOAc (100 mL) and washed with H2O (2×50 mL) and brine (50 mL). The organic layer was dried over sodium sulfate, and the solvent was removed in vacuuo to afford the desired 1-{4-[3-(diethylamino)propoxy]phenyl}ethanone. The crude alkylated product was used for further transformation after purifying using silica gel column chromatography (1-4% MeOH/DCM).
Workup
- additionwas added to the reaction mixture
- temperatureAfter cooling to rt
- customthe reaction mixture was quenched
- additionby treating the mixture with saturated sodium bicarbonate
- additionThe aqueous layer was poured into EtOAc (100 mL)
- washwashed with H2O (2×50 mL) and brine (50 mL)
- dry with materialThe organic layer was dried over sodium sulfate
- customthe solvent was removed in vacuuo
Sources & evidence
- ORD record
- ord-175e214a08d84fa8818c72f8b93ccfd3
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737285B2
Linked notes
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