Reaction #1256743

ord-b92f8a893a6b4bbb9a3f7e70a4b33521

Reaction equation

[Cl-].[NH4+]
ammonium chloride
CCCCC
n-pentane
CC(C)[SiH](Cl)C(C)C
Diisopropylchlorosilane
C1CCOC1
THF
CC(C)C[SiH](C(C)C)C(C)C
Isobutyldiisopropylsilane

Conditions

Temperature
70°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.WAITThe reaction mixture was left
  2. 2
    Temperatureto cool
  3. 3
    WashThe formed organic layer was washed three times with water
  4. 4
    Dryingby drying over sodium sulfate anhydrate
  5. 5
    OtherThe solvent was removed
  6. 6
    workup.DISTILLATIONfollowed by purification through distillation under reduced pressure, whereby the Compound 40a
  7. 7
    Otherwas obtained as a colorless liquid (boiling point; 70 mmHg, 102 to 106° C. fraction, 8.26 g, 50%)

Procedure

Diisopropylchlorosilane (16.4 mL, 96.1 mmol) was dissolved in THF (100 mL), and isobutylmagnesium bromide THF solution (1.0M, 100 mL) was added dropwise thereto under nitrogen for 30 minutes. Subsequently, cuprous bromide (286 mg, 2.00 mmol) was added to the resultant mixture, followed by stirring at 70° C. overnight. The reaction mixture was left to cool, and saturated aqueous ammonium chloride and n-pentane were added thereto. The formed organic layer was washed three times with water and once with saturated brine, followed by drying over sodium sulfate anhydrate. The solvent was removed, followed by purification through distillation under reduced pressure, whereby the Compound 40a was obtained as a colorless liquid (boiling point; 70 mmHg, 102 to 106° C. fraction, 8.26 g, 50%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07825103B2uspto-grants-2010_11