Water → 4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzylamine
Reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC>[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 8.2 g (26 millimoles) of 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-ethynyl]-benzonitrile (Example 1) in 150 ml of absolute ether was added dropwise to a suspension of 2.8 g (73 millimoles) of lithium aluminum hydride in 150 ml of absolute ether at room temperature in the course of 25 minutes. The mixture was stirred under reflux for 3.5 hours and then cooled, after which water was added carefully, sodium sulfate solution was added dropwise and the phases were separated. The aqueous phase was extracted twice with ether, and the combined ether phases were washed once with water, dried over Na2SO4 and evaporated down. 7.7 g (93%) of the title compound of melting point 84°-88° C. remained.
Workup
- temperatureunder reflux for 3.5 hours
- temperaturecooled
- customthe phases were separated
- extractionThe aqueous phase was extracted twice with ether
- washthe combined ether phases were washed once with water
- dry with materialdried over Na2SO4
- customevaporated down
Sources & evidence
- ORD record
- ord-e3e7d8c6b09a4b24a5958ed66d87a4d3
- Source dataset
- uspto-grants-1989_02
- Patent number
- US04806558
Reaction notes
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