Tetrahydrofuran → 2'-Hydroxy-4',6'-bis(methoxymethoxy)-3'-(2-propenyl)acetophenone
Reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH:9]=[CH2:10])=[C:6]([OH:11])[CH:5]=[C:4]([OH:12])[C:3]=1[C:13](=[O:15])[CH3:14].C(N(CC)C(C)C)(C)C.[CH3:25][O:26][CH3:27].[O:28]1[CH2:32]CC[CH2:29]1>>[OH:1][C:2]1[C:7]([CH2:8][CH:9]=[CH2:10])=[C:6]([O:11][CH2:25][O:26][CH3:27])[CH:5]=[C:4]([O:12][CH2:29][O:28][CH3:32])[C:3]=1[C:13](=[O:15])[CH3:14]Participants
Procedure
In 160 ml of anhydrous tetrahydrofuran were dissolved 18.4 g of the so-obtained 2',4',6'-trihydroxy3'-(2-propenyl)acetophenone and 57.1 g of N,N-diisopropylethylamine, and 28.4 g of chrolomethyl methyl ether was added to the solution under ice cooling and the reaction mixture was stirred under ice cooling for 1 hour, and further, stirred at room temperature for 4 hours to effect a reaction. The reaction mixture was extracted with diethyl ether and filtered, and the solvent was removed from the filtrate by distillation. The obtained residue was subjected to the silica gel column chromatography [eluting solvent=n-hexane/ethyl acetate (7/1)] to obtain 24.8 g (yield=94.7%) of 2'-hydroxy-4',6'-bismethoxymethoxy-3'-(2-propenyl)acetophenone in the form of a colorless oil.
Workup
- additionwas added to the solution under ice cooling
- stirringfurther, stirred at room temperature for 4 hours
- customa reaction
- extractionThe reaction mixture was extracted with diethyl ether
- filtrationfiltered
- customthe solvent was removed from the filtrate by distillation
- washThe obtained residue was subjected to the silica gel column chromatography [eluting solvent=n-hexane/ethyl acetate (7/1)]
Sources & evidence
- ORD record
- ord-7a22d84775e5409a8259bce92fa8e549
- Source dataset
- uspto-grants-1992_04
- Patent number
- US05106871
Reaction notes
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