Sodium Acetate → Acetic acid 2-(2-ethoxy-naphthalen-1-yl)-2-oxo-ethyl ester
Reaction equation
Br[CH2:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[O:15][CH2:16][CH3:17])=[O:4].[C:18]([O-:21])(=[O:20])[CH3:19].[Na+]>CN(C)C=O>[CH2:16]([O:15][C:6]1[CH:7]=[CH:8][C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]=1[C:3](=[O:4])[CH2:2][O:21][C:18](=[O:20])[CH3:19])[CH3:17]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 2-bromo-1-(2-ethoxy-naphthalen-1-yl)-ethanone (7.0 g), sodium acetate (2.0 g) and N,N-dimethylformamide (80 mL) was heated at 80° C. for 1.5 hours. After cooling to room temperature the N,N-dimethylformamide was removed under reduced pressure and the resulting residue was partitioned between dichloromethane (60 mL) and water (60 mL). The organic phase was washed with water (60 mL), brine (60 mL), dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to afford acetic acid 2-(2-ethoxy-naphthalen-1-yl)-2-oxo-ethyl ester (6.1 g, 94%) as dark red oil. 1H NMR (CDCl3): 1.45 (3H, t, J=7.0 Hz), 2.2 (3H, s), 4.2 (2H, q, J=7.0 Hz), 5.15 (2H, s), 7.2 (1H, d, J=9.4 Hz), 7.35 (1H, m), 7.45 (1H, m), 7.75 (1H, d, J=8.1 Hz), 7.85 (2H, m).
Workup
- customwas removed under reduced pressure
- customthe resulting residue was partitioned between dichloromethane (60 mL) and water (60 mL)
- washThe organic phase was washed with water (60 mL), brine (60 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customthe solvent removed under reduced pressure
Sources & evidence
- ORD record
- ord-57ef121f30984db79b7ad37dc62c324e
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07429607B2
Reaction notes
Loading…