(3-Bromopropoxy)(tert-butyl)dimethylsilane → HCID 22449039, compound

HRID 2186730Notes

Reaction equation

HRID 2186730 reaction equation
[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11](C3CCCCO3)[C:5]=2[O:4][CH2:3]1.C[C:19]([CH3:22])([O-:21])C.[K+].[Si:24]([O:31][CH2:32][CH2:33][CH2:34]Br)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>CN(C=O)C.C(OCC)(=O)C>[Si:24]([O:31][CH2:32][CH2:33][CH2:34][N:7]1[C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([O:4][CH:5]3[CH2:6][CH2:8][CH2:22][CH2:19][O:21]3)[C:5]=2[O:4][CH2:3][C:2]1=[O:1])([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 22448949HCID 22448949, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22449039HCID 22449039, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

3-oxo-8-(tetrahydropyran-2-yl)-3,4-dihydro-2H-1,4-benzoxazine (2.0 g) was dissolved in DMF (25 ml), and potassium t-butoxide (1.1 g) was added to the resultant solution, and the mixture was stirred at 0° C. for 15 minutes and then at room temperature for 15 minutes. The reaction solution was cooled to 0° C., and 3-(tert-butyldimethylsilyloxy)-1-bromopropane (2.1 ml) was then added to the reaction solution, and the mixture was stirred for 3 hours at room temperature. The reaction solution was diluted with ethyl acetate, washed with a saturated ammonium chloride aqueous solution and saturated brine, and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the resultant residue was purified by column chromatography (silica gel:ethyl acetate/n-hexane=3:17) to obtain the object compound (2.55 g, yield 75%).

Workup

  1. waitat room temperature for 15 minutes
  2. temperatureThe reaction solution was cooled to 0° C.
  3. stirringthe mixture was stirred for 3 hours at room temperature
  4. washwashed with a saturated ammonium chloride aqueous solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThen, the solvent was distilled off under reduced pressure
  7. customthe resultant residue was purified by column chromatography (silica gel:ethyl acetate/n-hexane=3:17)

Sources & evidence

ORD record
ord-5cd16f8bc2eb45188d36a0afea900027
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

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