Hydrochloric Acid → 4-(1-Hydroxy-propyl)-3,8-dimethoxy-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:23]=[O:24])=[C:17]([O:21][CH3:22])[CH:18]=[C:19]([CH3:20])[C:12]=3[C:11](=[O:25])[O:10][C:9]=2[C:8]([CH3:26])=[C:7]([O:27][CH3:28])[CH:6]=1)=[O:4].Cl.O1CC[CH2:32][CH2:31]1>>[CH3:1][O:2][C:3]([C:5]1[C:15]2[O:14][C:13]3[C:16]([CH:23]([OH:24])[CH2:31][CH3:32])=[C:17]([O:21][CH3:22])[CH:18]=[C:19]([CH3:20])[C:12]=3[C:11](=[O:25])[O:10][C:9]=2[C:8]([CH3:26])=[C:7]([O:27][CH3:28])[CH:6]=1)=[O:4]Participants
4
Reactant 3
Product 1
Procedure
The compound from Example 3 (0.15 mmol) was dissolved in absolute tetrahydrofuran. A solution of 2M Grignard reagent (0.7 ml, 1.4 mmol) in tetrahydrofuran was added under ice bath. The mixture was stirred for 1 h. Upon completion, 2 ml of 1N hydrochloric acid was added, and the mixture was extracted with methylene chloride. The organic layer was subsequently washed with water and saturated brine, dried over anhydrous MgSO4, filtered and evaporated by a rotatory evaporator. After chromatographic purification on silica, the title compound was obtained.
Workup
- extractionthe mixture was extracted with methylene chloride
- washThe organic layer was subsequently washed with water and saturated brine
- dry with materialdried over anhydrous MgSO4
- filtrationfiltered
- customevaporated by a rotatory evaporator
- customAfter chromatographic purification on silica
Sources & evidence
- ORD record
- ord-529d19641b954efba2f38d9d24791ed3
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158623B2
Reaction notes
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