Ammonia → 8-(2-Furyl)-1,1,1,8-tetramethoxy-5-octyne
Reaction equation
[NH2-].[Li+].N.[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[CH:9]([O:13][CH3:14])[CH2:10][C:11]#[CH:12].Br[CH2:16][CH2:17][CH2:18][C:19]([O:24][CH3:25])([O:22][CH3:23])[O:20][CH3:21]>O1CCCC1>[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[CH:9]([O:13][CH3:14])[CH2:10][C:11]#[C:12][CH2:16][CH2:17][CH2:18][C:19]([O:24][CH3:25])([O:22][CH3:23])[O:20][CH3:21]Participants
Procedure
To a stirred solution of 4.09 g of lithium amide and 200 ml of liquid ammonia was added dropwise a solution of 24.3 g of 4-(2-furyl)-4-methoxy-1-butyne in 20 ml of tetrahydrofuran during 10 minutes. The mixture was stirred under reflux for 30 minutes and then treated dropwise with a solution of 40.4 g of 1-bromo-4,4,4-trimethoxybutane (U.S. Pat. No. 3,864,387) in 40 ml of tetrahydrofuran during 10 minutes. This solution was stirred under reflux for 60 minutes, the ammonia was allowed to evaporate over one hour and the resulting solution stirred at 20° C. for 10 minutes. The solution was then partitioned between ether and water, the organic layer separated, washed with brine, dried and concentrated, giving 58 g of crude 8-(2-furyl)-1,1,1,8-tetramethoxy-5-octyne as a liquid.
Workup
- temperatureunder reflux for 30 minutes
- stirringThis solution was stirred
- temperatureunder reflux for 60 minutes
- customto evaporate over one hour
- stirringthe resulting solution stirred at 20° C. for 10 minutes
- customThe solution was then partitioned between ether and water
- customthe organic layer separated
- washwashed with brine
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-06fbead8ec41433f996633ea0357d336
- Source dataset
- uspto-grants-1990_09
- Patent number
- US04958037
Reaction notes
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