Sodium Azide → cis-2-Azido-6-methoxy-1-phenyl-1,2,3,4-tetrahydronaphthalene
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C@@H:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C@H:8](OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:7][CH2:6]2.[N-:30]=[N+:31]=[N-:32].[Na+].C1OCCOCCOCCOCCOC1>CN(C)C=O>[N:30]([C@H:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C@H:9]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[N+:31]=[N-:32]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A N,N-dimethylformamide solution (50 mL) of crude trans-6-methoxy-1-phenyl-2-(4-methylbenzenesulfonyl)oxy-1,2,3,4-tetrahydronaphthalene 30 (3.4 g), sodium azide (3.78 g, 58.3 mmol) and 15-crown-5 (6.61 mL, 33.2 mmol) was heated at 75° C. for 7 h. The reaction mixture was poured into ice water (200 mL), and the product was extracted into diethyl ether (3×50 mL). The organic extracts were combined and washed successively with water (4×100 mL) and a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. The solvent was evaporated in vacuo, and the remaining residue was purified by medium pressure chromatography using 3% ethyl acetate in hexanes as the eluent to give crude cis-2-azido-6-methoxy-1-phenyl-1,2,3,4-tetrahydronaphthalene 31 (1.35 g, ~62%) as an oil which was used without further purification in the subsequent step.
Workup
- extractionthe product was extracted into diethyl ether (3×50 mL)
- washwashed successively with water (4×100 mL)
- dry with materiala saturated aqueous solution of sodium chloride, and dried over sodium sulfate
- customThe solvent was evaporated in vacuo
- customthe remaining residue was purified by medium pressure chromatography
Sources & evidence
- ORD record
- ord-9079d54aad694bd095f09c2d4107f75e
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06140354
Reaction notes
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