Dimethylformamide → 2-Propynyl 4-(2-propynyloxy)-3,5-dimethoxybenzoate
Reaction equation
CN(C=O)C.[OH:6][C:7]1[C:15]([O:16][CH3:17])=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[O:18][CH3:19].[CH2:20](Br)[C:21]#[CH:22].[C:24](=O)([O-])[O-].[K+].[K+].C(O[CH2:34][CH3:35])(=O)C>>[CH2:20]([O:6][C:7]1[C:8]([O:18][CH3:19])=[CH:9][C:10]([C:11]([O:13][CH2:24][C:34]#[CH:35])=[O:12])=[CH:14][C:15]=1[O:16][CH3:17])[C:21]#[CH:22]Participants
6
Conditions
- Temperature
- 80 °C
Procedure
To 100 ml of DMF were added 11.8 g of 4-hydroxy-3,5-dimethoxybenzoic acid, 15.7 g of propargyl bromide and 18 g of potassium carbonate, and the mixture obtained was stirred at room temperature for 8 hours and at 80° C. for 4 hours. Then, ethyl acetate was added to the reaction mixture and the mixture was filtered through Celite. Water and dilute hydrochloric acid were added to the filtrate in order and it was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The crystals obtained were washed with a mix solvent of hexane and MTBE to obtain 15.5 g of 2-propynyl 4-(2-propynyloxy)-3,5-dimethoxybenzoate represented by the formula:
Workup
- customthe mixture obtained
- filtrationthe mixture was filtered through Celite
- additionWater and dilute hydrochloric acid were added to the filtrate in order and it
- extractionwas extracted with ethyl acetate
- dry with materialThe organic layer was dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe crystals obtained
- washwere washed with a mix solvent of hexane and MTBE
Sources & evidence
- ORD record
- ord-500b451a3cf34c089770d0d107c25a51
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07714168B2
Reaction notes
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