Water → 4-Formyl-3,8-dimethoxy-1,9-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepine-6-carboxylic acid methyl ester
Reaction equation
[CH3:1][C:2]1[C:7]2[C:8]([O:10][C:11]3[C:12]([CH3:23])=[C:13]([O:21][CH3:22])[CH:14]=[C:15](C(O)=O)[C:16]=3[O:17][C:6]=2[C:5]([CH:24]=[O:25])=[C:4](O)[CH:3]=1)=[O:9].[C:27]([O-:30])([O-:29])=O.[K+].[K+].[CH3:33]I.O.CN([CH:39]=[O:40])C>>[CH3:33][O:29][C:27]([C:15]1[C:16]2[O:17][C:6]3[C:5]([CH:24]=[O:25])=[C:4]([O:40][CH3:39])[CH:3]=[C:2]([CH3:1])[C:7]=3[C:8](=[O:9])[O:10][C:11]=2[C:12]([CH3:23])=[C:13]([O:21][CH3:22])[CH:14]=1)=[O:30]Participants
6
Procedure
Psoromic acid (1 mmol) was dissolved in DMF (10 mL), K2CO3 (2.4 mmol) was added and stirred for several minutes at room temperature. Then, CH3I (2.4 mmol) were added. The reaction mixture was maintained at 40° C. and monitored by TLC. Upon completion, the reaction mixture was poured into 50 mL of water and extracted with ethyl acetate. The organic layer was subsequently washed with saturated NaHCO3 solution and saturated brine, dried over anhydrous MgSO4, evaporated by a rotatory evaporator and purified by column chromatography to give a white solid product.
Workup
- temperatureThe reaction mixture was maintained at 40° C.
- extractionextracted with ethyl acetate
- washThe organic layer was subsequently washed with saturated NaHCO3 solution and saturated brine
- dry with materialdried over anhydrous MgSO4
- customevaporated by a rotatory evaporator
- custompurified by column chromatography
- customto give a white solid product
Sources & evidence
- ORD record
- ord-45259b44a91a4abda6458718f9c61499
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158623B2
Reaction notes
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