1,3-Di-tert-butyl-2-chloro-2,3-dihydro-1H-1,3,2-diazasilole → HCID 123717700, compound

HRID 2273174Notes

Reaction equation

HRID 2273174 reaction equation
Cl[SiH:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[CH:5]=[CH:4][N:3]1[C:11]([CH3:14])([CH3:13])[CH3:12].O1C[CH2:18][CH2:17][CH2:16]1.C=C([Mg]Br)C>CCCCCC>[C:11]([N:3]1[CH:4]=[CH:5][N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[SiH:2]1[C:17]([CH3:18])=[CH2:16])([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 713346111,3-Di-tert-butyl-2-chloro-2,3-dihydro-1H-1,3,2-diazasiloleHCID 178420658HCID 178420658, compound

Product 1

HCID 123717700HCID 123717700, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

In an argon atmosphere, 8.71 g (37.4 mmol) of Si(tBuNCHCHNtBu)(H)Cl was dissolved in 20 mL of hexane and after adding a (prop-1-en-2-yl)magnesium bromide tetrahydrofuran solution (0.57 mol/L, 69.0 mL, 39.3 mmol), the resulting solution was refluxed for 14 hours. Insoluble matters produced were separated by filtration, and the solvent was removed by distillation from the filtrate under atmospheric pressure. The obtained residue was distilled under reduced pressure (distillation temperature: 80° C./4.3×102 Pa) to obtain 1,3-di-tert-butyl-2-(prop-1-en-2-yl)-1,3-diaza-2-silacyclopent-4-ene (Si(tBuNCHCHNtBu)(H)C(CH3)CH2) as a yellow liquid (yielded amount: 4.18 g, yield: 47%).

Workup

  1. temperaturethe resulting solution was refluxed for 14 hours
  2. customInsoluble matters produced
  3. customwere separated by filtration
  4. customthe solvent was removed by distillation from the filtrate under atmospheric pressure
  5. distillationThe obtained residue was distilled under reduced pressure (distillation temperature: 80° C./4.3×102 Pa)
  6. customto obtain

Sources & evidence

ORD record
ord-ec5e4838d70f430f913a09a8d90a057e
Source dataset
uspto-grants-2015_09
Patent number
US09120825B2

Reaction notes

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