Sodium Bicarbonate → HCID 15671161, compound
Reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[Cl:15])[O:11][C:10]([CH3:27])([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=1)[CH2:9][C:8]2=[O:28])(=[O:3])[CH3:2].C(=O)(O)[O-].[Na+]>C(O)(=O)C.[Zn]>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[Cl:15])[O:11][C:10]([CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=1)([CH3:27])[CH2:9][C:8]2=[O:28])(=[O:3])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
1 g of zinc powder was added in portions to a solution of 740 mg of 6 -acetoxy-7-chloro-2-methyl-2-(4-nitrophenoxymethyl)-4-oxochroman (prepared as described in Preparation 35) dissolved in 15 ml of acetic acid. The reaction mixture was stirred for 2 hours, after which it was poured into a saturated aqueous solution of sodium bicarbonate whilst ice-cooling, and the mixture was then extracted with benzene. The extract was washed with water and dried over anhydrous sodium sulfate, after which the solvent was removed by evaporation under reduced pressure. The residue was subjected to column chromatography through silica gel, eluted with a 1:1 by volume mixture of benzene and ethyl acetate, to afford 280 mg of the title compound as a pale yellow oil.
Workup
- temperaturecooling
- extractionthe mixture was then extracted with benzene
- washThe extract was washed with water
- dry with materialdried over anhydrous sodium sulfate
- customafter which the solvent was removed by evaporation under reduced pressure
- washeluted with a 1:1 by volume mixture of benzene and ethyl acetate
Sources & evidence
- ORD record
- ord-48d4d4802f7b4f3fb1c80947f1a9dc79
- Source dataset
- uspto-grants-1989_10
- Patent number
- US04873255
Reaction notes
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