Hydrochloric Acid → 5-[5-(4-Cyanophenoxy)pentyl]-3-methylisoxazole
Reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[O:4][N:3]=1.C([Li])CCC.Br[CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1.[Cl-].[Na+].Cl>O1CCCC1.C(OCC)(=O)C>[C:23]([C:22]1[CH:25]=[CH:26][C:19]([O:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:7][C:5]2[O:4][N:3]=[C:2]([CH3:1])[CH:6]=2)=[CH:20][CH:21]=1)#[N:24]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -70 °C
Procedure
To a solution of 5.86 g of 3,5-dimethylisoxazole in 120 ml of dry tetrahydrofuran at -70° C. under nitrogen was added during 14 minutes 36 ml of n-butyllithium (1.7M in hexane). The mixture was stirred at -70° C. for 30 minutes, and then 15.2 g of 4-(4-bromobutyloxy)benzonitrile in 40 ml of tetrahydrofuran was added over a 15 minute period. The reaction mixture was stirred for 1.5 hours at -70° C. and then allowed to warm to room temperature and stirred for 2.5 hours longer. Evaporation of the solvent gave a residue which was treated with 300 ml of ethyl acetate, 150 ml of concentrated sodium chloride solution and 12 ml of hydrochloric acid. The material which was soluble in ethyl acetate was isolated, combined with material from another run of the same scale and subjected to high pressure liquid chromatography with ether-hexane (1:1) to give 20 g of 5-[5-(4-cyanophenoxy)pentyl]-3-methylisoxazole as a colorless solid, m.p. 57° C.
Workup
- stirringThe reaction mixture was stirred for 1.5 hours at -70° C.
- temperatureto warm to room temperature
- stirringstirred for 2.5 hours longer
- customEvaporation of the solvent
- customgave a residue which
- customwas isolated
Sources & evidence
- ORD record
- ord-dccbec380b394e08bd2f8a458be4eca4
- Source dataset
- uspto-grants-1989_06
- Patent number
- US04843087
Reaction notes
Loading…