Methyl iodide → 4-formyl-3-hydroxy-8-methoxy-1,9-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepine-6-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:15]2[O:14][C:13]3[C:16]([CH:22]=[O:23])=[C:17]([OH:21])[CH:18]=[C:19]([CH3:20])[C:12]=3[C:11](=[O:24])[O:10][C:9]=2[C:8]([CH3:25])=[C:7]([OH:26])[CH:6]=1)=[O:4].[C:27]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[C:15]2[O:14][C:13]3[C:16]([CH:22]=[O:23])=[C:17]([OH:21])[CH:18]=[C:19]([CH3:20])[C:12]=3[C:11](=[O:24])[O:10][C:9]=2[C:8]([CH3:25])=[C:7]([O:26][CH3:27])[CH:6]=1)=[O:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1 mmol of 4-Formyl-3,8-dihydroxy-1,9-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepine-6-carboxylic acid methyl ester was dissolved in 3 mL of acetone, 1 mmol K2CO3 was added and stirred for several minutes. Then, 1 mmol of CH3I in acetone was added from a pressure-equalizing dropping funnel. The reaction mixture was monitored by TLC. Upon completion, the reaction mixture was filtered to remove K2CO3 and evaporated by a rotatory evaporator to remove acetone. The residue was purified by column chromatography to give 4-formyl-3-hydroxy-8-methoxy-1,9-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepine-6-carboxylic acid methyl ester (84%).
Workup
- filtrationUpon completion, the reaction mixture was filtered
- customto remove K2CO3
- customevaporated by a rotatory evaporator
- customto remove acetone
- customThe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-17d29001286e41d58c834174ebd3db37
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158623B2
Reaction notes
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