Ammonia → 2,5-Dihydro-2,5-dimethoxy-2-(8,8,8-trimethoxy-3-octynyl)furan
Reaction equation
[NH2-].[Li+].N.[CH3:4][O:5][C:6]1([CH2:13][CH2:14][C:15]#[CH:16])[CH:10]=[CH:9][CH:8]([O:11][CH3:12])[O:7]1.Br[CH2:18][CH2:19][CH2:20][C:21]([O:26][CH3:27])([O:24][CH3:25])[O:22][CH3:23]>O1CCCC1>[CH3:4][O:5][C:6]1([CH2:13][CH2:14][C:15]#[C:16][CH2:18][CH2:19][CH2:20][C:21]([O:26][CH3:27])([O:24][CH3:25])[O:22][CH3:23])[CH:10]=[CH:9][CH:8]([O:11][CH3:12])[O:7]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred mixture of 0.51 g of lithium amide and ml of liquid ammonia was added dropwise a solution of 3.64 g of 2,5-dihydro-2,5-dimethoxy-2-(3-butynyl)furan in 2.5 ml of tetrahydrofuran during 5 minutes. The mixture was stirred under reflux for 30 minutes and then treated dropwise with a solution of 5.0 g of 1-bromo-4,4,4-trimethoxybutane (U.S. Pat. No. 3,864,387) in 5 ml of tetrahydrofuran during 5 minutes. This solution was stirred under reflux for one hour, the ammonia allowed to evaporate during one hour and the resulting solution stirred at 20° C. for 10 minutes. This solution was partitioned with ether and brine. The organic layer was dried, treated with 2 drops of pyridine, and then concentrated, giving 7.1 g of the desired compound as a light amber oil; PMR δ 5.9 (2H, m, vinyl hydrogens).
Workup
- temperatureunder reflux for 30 minutes
- stirringThis solution was stirred
- temperatureunder reflux for one hour
- customto evaporate during one hour
- stirringthe resulting solution stirred at 20° C. for 10 minutes
- customThis solution was partitioned with ether and brine
- customThe organic layer was dried
- additiontreated with 2 drops of pyridine
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ade4828b740c429e9484a8d1b2ed028f
- Source dataset
- uspto-grants-1990_09
- Patent number
- US04958037
Reaction notes
Loading…