Bis(dimethylamino)dimethylsilane → 3,3,6,6,9,9-Hexamethyl-1,2,4,5-tetraoxa-3-silacyclononane

HRID 971831Notes

Reaction equation

[CH3:1][C:2]([O:11][OH:12])([CH2:4][CH2:5][C:6]([CH3:10])([O:8][OH:9])[CH3:7])[CH3:3].CN([Si:16](N(C)C)([CH3:18])[CH3:17])C>CCOCC>[CH3:17][Si:16]1([CH3:18])[O:12][O:11][C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]([CH3:10])([CH3:7])[O:8][O:9]1

Participants

Conditions

Temperature: 16 °C

Procedure

Into a 250 ml flask equipped with a magnetic stirring bar, addition funnel and calcium sulfate drying tube is placed a solution of 10.84g (0.06 mole, 98.66% pure) of 2,5-dimethyl-2,5-dihydroperoxyhexane in 120 ml of anhydrous ether. The solution is cooled to 16° C. and a solution of 8.77g (0.06 mole) of bis(dimethylamino) dimethylsilane in 30 ml of anhydrous ether is added slowly dropwise. The reaction temperature is maintained between 15° and 20° by use of an ice bath and by adjusting the rate of addition. After the addition is complete, the solution is stirred at room temperature for one hour. The solution is filtered to remove a small amount of suspended solid. The solvent is removed by distillation yielding 13.75g of 3,3,6,6,9,9-hexamethyl-1,2,4,5-tetraoxa-3-silacyclononane (theoretical yield 14.05g, 97.9%; A.O. analysis 13.32%, theoretical 13.67%, 97.4% pure). The infrared spectrum of the reaction product of this example is identical to the spectrum of material produced in Example 1.

Workup

customInto a 250 ml flask equipped with a magnetic stirring bar, addition funnel and calcium sulfate drying tube
temperatureThe reaction temperature is maintained between 15° and 20° by use of an ice bath
additionthe rate of addition
additionAfter the addition
filtrationThe solution is filtered
customto remove a small amount of suspended solid
customThe solvent is removed by distillation

Sources & evidence

ORD record: ord-ce90ff2921424486a3dd2f34914212c2
Source dataset: uspto-grants-1979_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04161485

Reaction notes

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