Chlorodi(isopropyl)silane → HCID 123518261, compound

HRID 1625174Notes

Reaction equation

HRID 1625174 reaction equation
[C:1]([Mg]Br)([CH3:3])=[CH2:2].[CH:6]([SiH:9]([CH:11]([CH3:13])[CH3:12])Cl)([CH3:8])[CH3:7]>C1COCC1>[C:1]([SiH:9]([CH:11]([CH3:13])[CH3:12])[CH:6]([CH3:8])[CH3:7])([CH3:3])=[CH2:2]

Participants

4

Reactant 2

HCID 2758383Chlorodi(isopropyl)silaneHCID 178456138HCID 178456138, compound

Product 1

HCID 123518261HCID 123518261, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

0.5 M isopropenylmagnesium bromide in THF (Aldrich, 320 mL, 160 mmol, 1.1 eq. to silane) was added dropwise at 0° C. to diisopropylchlorosilane (22 g, 145 mmol) in anhydrous THF (40 mL). The reaction mixture was heated to 40° C. for 8 hours, then cooled and quenched with water (50 mL) and dilute sulfuric acid (50 mL). The crude product was extracted into pentane, washed with water and brine, dried over MgSO4, filtered and concentrated. Careful removal of solvent (product is volatile) yielded 22 g of crude isopropenyldiisopropylsilane as a pale yellow liquid that was not subjected to further purification.

Workup

  1. temperaturecooled
  2. customquenched with water (50 mL) and dilute sulfuric acid (50 mL)
  3. extractionThe crude product was extracted into pentane
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customCareful removal of solvent (product is volatile)

Sources & evidence

ORD record
ord-440e344a22fa4aeca050d5de2bb5075f
Source dataset
uspto-grants-2014_07
Patent number
US08779179B2

Reaction notes

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