Sodium Hydroxide → Trans-2,3,5,6,7,8-hexahydro-8-hydroxy-7-(N-propylamino)naphtho[2,3-b]thiophene
Reaction equation
[OH:1][C@@H:2]1[C:14]2[C:6](=[CH:7][C:8]3[CH2:12][CH2:11][S:10][C:9]=3[CH:13]=2)[CH2:5][CH2:4][C@H:3]1[NH:15][C:16](=O)[CH2:17][CH3:18].[OH-].[Na+]>O1CCCC1.O>[OH:1][C@@H:2]1[C:14]2[C:6](=[CH:7][C:8]3[CH2:12][CH2:11][S:10][C:9]=3[CH:13]=2)[CH2:5][CH2:4][C@H:3]1[NH:15][CH2:16][CH2:17][CH3:18]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
In a 500 ml three-necked flask fitted with a magnetic stirrer and a nitrogen inlet, 2.3 g (61 mmol) of AILiH4 are suspended in 75 ml of dry tetrahydrofuran. 6.2 g (24.5 mmol) of the product obtained in Step 2 dissolved in 97 ml of dry tetrahydrofuran are slowly added at room temperature. After 18 hours' stirring at room temperature, the reaction is stopped by the addition of 1.6 ml of water, 1.3 ml of 20 % NaOH in water and finally 5.8 ml of water in succession. The reaction mixture is stirred for 0.5 hour at room temperature and then filtered. The precipitate is washed copiously with tetrahydrofuran and the flitrate is concentrated in vacuo to yield 1.37 g of the expected product in the form of a meringue, Yield: 97 %.
Workup
- customIn a 500 ml three-necked flask fitted with a magnetic stirrer and a nitrogen inlet
- additionare slowly added at room temperature
- stirringThe reaction mixture is stirred for 0.5 hour at room temperature
- filtrationfiltered
- washThe precipitate is washed copiously with tetrahydrofuran
- concentrationthe flitrate is concentrated in vacuo
Sources & evidence
- ORD record
- ord-04b5894104d743daa3447f348afad5c1
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05733908
Reaction notes
Loading…