Triethylamine → HCID 79353504, compound
Reaction equation
Br[CH2:2][CH2:3][C:4]([CH3:7])([OH:6])[CH3:5].C(N(CC)CC)C.[N-:15]=[N+:16]=[N-:17].[Na+]>C(Cl)Cl.O>[N:15]([CH2:2][CH2:3][C:4]([CH3:7])([OH:6])[CH3:5])=[N+:16]=[N-:17]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a mixture of 4-bromo-2-methylbutan-2-ol (0.4 g, 2.4 mmol) and triethylamine (1 ml, 7 mmol, 3 eq.) in CH2Cl2 (15 ml) was added sodium azide (0.47 g, 7 mmol, 3 eq.) in H2O (5 ml) and the mixture was allowed to stir overnight. The mixture was quenched with water and extracted with CH2Cl2 (3×50 ml). The combined organic layer was washed with water, brine and dried over sodium sulphate. The solvent was distilled off to afford the product in 65% yield (0.2 g). 1H NMR (300 MHz, DMSO-d6): δ 4.39 (br s, 1H), 3.40-3.32 (m, 2H), 1.15 (t, 2H), 1.23-1.04 (m, 6H).
Workup
- customThe mixture was quenched with water
- extractionextracted with CH2Cl2 (3×50 ml)
- washThe combined organic layer was washed with water, brine
- dry with materialdried over sodium sulphate
- distillationThe solvent was distilled off
- customto afford the product in 65% yield (0.2 g)
Sources & evidence
- ORD record
- ord-dd7b74afc2384757924d3becd2a98537
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447091B2
Reaction notes
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