Potassium Carbonate → (E)-N-ethyl-N-(6-methoxy-6-methyl-2-hepten-4-ynyl)-5-formyl-2-furylmethylamine
Reaction equation
O[CH2:2][C:3]1[O:7][C:6]([CH:8]=[O:9])=[CH:5][CH:4]=1.P(Br)(Br)Br.C(=O)([O-])[O-].[K+].[K+].Cl.[CH2:21]([NH:23][CH2:24]/[CH:25]=[CH:26]/[C:27]#[C:28][C:29]([O:32][CH3:33])([CH3:31])[CH3:30])[CH3:22]>C(OCC)C.CN(C)C=O>[CH2:21]([N:23]([CH2:2][C:3]1[O:7][C:6]([CH:8]=[O:9])=[CH:5][CH:4]=1)[CH2:24]/[CH:25]=[CH:26]/[C:27]#[C:28][C:29]([O:32][CH3:33])([CH3:30])[CH3:31])[CH3:22]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
0.36 g of 5-hydroxymethyl-2-furaldehyde was dissolved in 10 ml of ethyl ether, and under a nitrogen atmosphere, a ethyl ether solution (2 ml) of 0.25 g of phosphorus tribromide was added dropwise at 0° C. After the mixture was stirred at room temperature for 30 minutes, 0.70 g of potassium carbonate and a dimethylformamide solution (15 ml) of 0.62 g of (E)-N-ethyl-6-methoxy-6-methyl-2-hepten-4-ynylamine hydrochloride were added. The mixture was stirred overnight at room temperature, and then worked up in a customary manner. The product was purified by silica gel column chromatography [hexane/ethyl acetate=2/1] to give 0.62 g of (E)-N-ethyl-N-(6-methoxy-6-methyl-2-hepten-4-ynyl)-5-formyl-2-furylmethylamine as a pale yellow oil.
Workup
- stirringThe mixture was stirred overnight at room temperature
- customThe product was purified by silica gel column chromatography [hexane/ethyl acetate=2/1]
Sources & evidence
- ORD record
- ord-13ad9b3f24bd425aafdec96e8841e640
- Source dataset
- uspto-grants-1994_04
- Patent number
- US05306728
Reaction notes
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