Tetrabutylammonium → 2-[[(2E)-4-Azido-2-methyl-2-buten-1-yl]oxy]tetrahydro-2H-pyran
Reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].C([N+](CCCC)(CCCC)CCCC)CCC.Cl[CH2:23]/[CH:24]=[C:25](\[CH3:34])/[CH2:26][O:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1>O.CCCCC>[N:1]([CH2:23]/[CH:24]=[C:25](\[CH3:34])/[CH2:26][O:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1)=[N+:2]=[N-:3]Participants
6
Procedure
A solution of 11.43 g (175.86 mmol) of sodium azide (NaN3) and 2.20 g (6.45 mmol) of tetrabutylammonium hydrogenosulfate in 60 ml of water was added to a solution of 12.0 g (58.62 mmol) of (E)-2-(4-Chloro-2-methylbut-2-en yloxy)tetrahydro-2H-pyran in 300 ml of pentane. The reaction mixture was stirred at room temperature overnight. The organic phase was separated and the aqueous phase was extracted with 3×150 ml of Et2O. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated to give 11.21 g (53.06 mmol, 90% yield) of a mixture of azides isomers. No purification was done as infeasible separation was observed on silica gel. The product was used without further purification for the next step.
Workup
- customThe organic phase was separated
- extractionthe aqueous phase was extracted with 3×150 ml of Et2O
- washThe combined organic phases were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-07ba0338d4bb4ebf96b200826f806e94
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07767842B2
Reaction notes
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