Carbon tetrabromide → 2-(5-Bromo-1,3-oxazol-2-yl)propan-2-yloxy-tert-butylsilane
Reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:14])([CH3:13])[C:8]1[O:9][CH:10]=[CH:11][N:12]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.C(Br)(Br)(Br)[Br:21]>O1CCCC1.[Cl-].[NH4+]>[Br:21][C:10]1[O:9][C:8]([C:7]([CH3:14])([CH3:13])[O:6][SiH2:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[N:12][CH:11]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -40 °C
Procedure
To a solution of 2-(tert-Butyl-dimethyl-silanyloxymethyl)-oxazole) (0.35 g, 1.643 mmol) in dry tetrahydrofuran (8 mL) is added n-Butyl lithium (0.26 g, 4.107 mmol) drop wise under nitrogen atmosphere at −78° C. then stirred at −40° C. for 2 hours. The reaction mixture is again cooled to −78° C. then added carbontetrabromide (1.36 g, 4.107 mmol) and stirred to room temperature for 14 hours. Reaction mixture is diluted with saturated ammonium chloride solution and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo and purified by column chromatography eluting 2% Ethyl acetate in hexane to afford the crude title compound (0.18 g), which is used in the next step without purification. LC-MS (m/z): [M+H]=294.2.
Workup
- temperatureThe reaction mixture is again cooled to −78° C.
- customReaction mixture
- extractionextracted with ethyl acetate
- dry with materialOrganic layer is dried over sodium sulphate, solvent
- customis evaporated in vacuo
- custompurified by column chromatography
- washeluting 2% Ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-e8120560d7104a98bf2f57e559d3bcac
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09340564B2
Reaction notes
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