Dimethylformamide → 2-Propynyl 4-(2-propynyloxy)-3-methoxybenzoate
Reaction equation
CN(C=O)C.[OH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[O:16][CH3:17].[CH2:18](Br)[C:19]#[CH:20].[C:22](=O)([O-])[O-].[K+].[K+].C(O[CH2:32][CH3:33])(=O)C>>[CH2:18]([O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([O:13][CH2:22][C:32]#[CH:33])=[O:12])=[CH:9][C:8]=1[O:16][CH3:17])[C:19]#[CH:20]Participants
Procedure
To 100 ml of DMF were added 10 g of 4-hydroxy-3-methoxybenzoic acid, 15.7 g of propargyl bromide and 18 g of potassium carbonate, and the resulting mixture was stirred at room temperature for 8 hours, and then at 80° C. for 2 hours. Thereafter, ethyl acetate was added to the reaction mixture which had been allowed to cool to near room temperature, and this was filtered through Celite (registered trade mark). To the filtrate were added sequentially water and dilute hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was dried with magnesium sulfate, and concentrated under reduced pressure. The resulting crystals were washed with a mixed solvent of hexane and MTBE, and 13.2 g of 2-propynyl 4-(2-propynyloxy)-3-methoxybenzoate was obtained.
Workup
- waitat 80° C. for 2 hours
- temperatureto cool to near room temperature
- filtrationthis was filtered through Celite (registered trade mark)
- additionTo the filtrate were added sequentially water and dilute hydrochloric acid
- extractionfollowed by extraction with ethyl acetate
- dry with materialThe organic layer was dried with magnesium sulfate
- concentrationconcentrated under reduced pressure
- washThe resulting crystals were washed with a mixed solvent of hexane and MTBE
Sources & evidence
- ORD record
- ord-d9dc0ac6b2374d3d99b18afd6c4ca319
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003699B2
Reaction notes
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