4-Ethynylbenzonitrile → 5-(4-Cyanophenyl)-3-(5,6,7,8-tetrahydro-3-methoxy-5,5,8,8-tetramethyl-2-naphthalenyl)-isoxazole
Reaction equation
Cl[O-].[Na+].[CH3:4][O:5][C:6]1[C:7]([CH:20]=[N:21][OH:22])=[CH:8][C:9]2[C:10]([CH3:19])([CH3:18])[CH2:11][CH2:12][C:13]([CH3:17])([CH3:16])[C:14]=2[CH:15]=1.[C:23]([C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=1)#[CH:24]>>[C:29]([C:28]1[CH:31]=[CH:32][C:25]([C:23]2[O:22][N:21]=[C:20]([C:7]3[C:6]([O:5][CH3:4])=[CH:15][C:14]4[C:13]([CH3:16])([CH3:17])[CH2:12][CH2:11][C:10]([CH3:18])([CH3:19])[C:9]=4[CH:8]=3)[CH:24]=2)=[CH:26][CH:27]=1)#[N:30]Participants
Procedure
17.2 g of a 10% strength aqueous sodium hypochlorite solution were added dropwise at 10°-15° C. to a solution of 5.0 g (19 millimoles) of 5,6,7,8-tetrahydro-3-methoxy-5,5,8,8-tetramethyl-2-naphthaldoxime and 2.4 g (19 millimoles) of 4-ethynylbenzonitrile. The mixture was stirred for 1.5 hours at room temperature. Thereafter, the reaction mixture was poured onto water, the phases were separated and the aqueous phase was extracted again with methylene chloride. The combined organic extracts were washed with sodium bisulfite solution, dried over sodium sulfate and evaporated down. The residue was digested in hot methanol, the mixture was allowed to cool and the crystals were filtered off under suction and dried to give 5.4 g of the title compound of melting point 202°-203° C.
Workup
- additionThereafter, the reaction mixture was poured onto water
- customthe phases were separated
- extractionthe aqueous phase was extracted again with methylene chloride
- washThe combined organic extracts were washed with sodium bisulfite solution
- dry with materialdried over sodium sulfate
- customevaporated down
- temperatureto cool
- filtrationthe crystals were filtered off under suction
- customdried
Sources & evidence
- ORD record
- ord-4ac78dbd00ec4b29aa87c1ac043b4e4a
- Source dataset
- uspto-grants-1995_12
- Patent number
- US05475017
Reaction notes
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