Ammonium Chloride → (E)-3-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-2-butenol
Reaction equation
[CH3:1][CH:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10](/[C:14](/[CH3:21])=[CH:15]/[C:16](OCC)=[O:17])=[CH:11][CH:12]=2)[CH2:7][CH2:6][CH2:5]1)[CH3:3].[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+]>O1CCCC1.C1(C)C=CC=CC=1>[CH3:3][CH:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10](/[C:14](/[CH3:21])=[CH:15]/[CH2:16][OH:17])=[CH:11][CH:12]=2)[CH2:7][CH2:6][CH2:5]1)[CH3:1]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -70 °C
Procedure
1.0 g of ethyl (E)-3-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-2-butenoate prepared in Example 1 was dissolved in 20 ml of tetrahydrofuran. The obtained solution was cooled to −70° C., followed by the gradual addition of 7.0 ml (10.5 mmol) of a 1.5 M solution of diisobutylaluminum hydride in toluene. The obtained mixture was stirred for 2 hours, followed by the addition of an aqueous solution of ammonium chloride. The obtained mixture was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and concentrated in a vacuum to give 650 mg of the title compound as a colorless oil.
Workup
- extractionThe obtained mixture was extracted with ethyl acetate
- washThe organic phase was washed with a saturated aqueous solution of common salt
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated in a vacuum
Sources & evidence
- ORD record
- ord-3644e59d641149bf889950bafc132add
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06420363B1
Reaction notes
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