Sodium hydride → 4-[2-(2-Naphthalenyl)-2-oxoethoxy]-alpha-oxobenzeneacetic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[H-].[Na+].[CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[C:26]([CH2:28]Br)=[O:27]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:28][C:26]([C:17]2[CH:18]=[CH:19][C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=2)=[O:27])=[CH:7][CH:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.50 g) in 5 mL of dimethylformamide was treated with 60% sodium hydride (0.112 g) and after 20 minutes, bromomethyl 2-naphthyl ketone (0.70 g) was added. The reaction mixture was stirred 3 hours at room temperature, was quenched with 0.1 mL of acetic acid and was diluted with ethyl acetate (75 mL). The mixture was washed with water (1 x 25 mL) and brine (1×25 mL), dried (MgSO4) and chromatographed over 100 g of silica gel, eluting with dichoromethane-ethyl acetate (50:1) to give 0.62 g of 4-[2-(2-naphthalenyl)-2-oxoethoxy]-alpha-oxobenzeneacetic acid methyl ester, mp 120°-121° C.
Workup
- customwas quenched with 0.1 mL of acetic acid
- additionwas diluted with ethyl acetate (75 mL)
- washThe mixture was washed with water (1 x 25 mL) and brine (1×25 mL)
- dry with materialdried (MgSO4)
- customchromatographed over 100 g of silica gel
- washeluting with dichoromethane-ethyl acetate (50:1)
Sources & evidence
- ORD record
- ord-c62095c34f4847e78cc2960ab942da62
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05344843
Reaction notes
Loading…