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Tetrahydrofuran → Triisopropylmethoxysilane

HRID 1678557
Notes
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Reaction equation

HRID 1678557 reaction equation
[CH2:1]1[CH2:5]OC[CH2:2]1.C([Mg]Cl)(C)C.[SiH4].[CH:12]([Si:15]([CH:19]([CH3:21])[CH3:20])([O:17][CH3:18])Cl)([CH3:14])[CH3:13]>C1(C)C=CC=CC=1>[CH:12]([Si:15]([CH:1]([CH3:2])[CH3:5])([CH:19]([CH3:21])[CH3:20])[O:17][CH3:18])([CH3:14])[CH3:13]
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 23953SilaneHCID 53833435HCID 53833435, compoundHCID 178418918HCID 178418918, compound2×

Product 1

HCID 589230Triisopropylmethoxysilane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent
2×

Conditions

Temperature
70 °C

Procedure

To the mixture of the silanes containing diisopropylmethoxychlorosilane as obtained from the disproportionation reaction in (b) above, was added 150 ml of toluene to dissolve the mixture, thereby to obtain a toluene solution of the said silane mixture. The THF solution of isopropyl magnesium chloride (Grignard reagent) as prepared in (a) above was added dropwise through a dropping funnel to the toluene solution of said silane mixture at 40° C.-50° C. over 1 hour. Then the resulting mixture was stirred at 70° C. for 4 hours. Thus, the Grignard reagent was reacted with the diisopropylmethoxychlorosilane contained in the said toluene solution, to produce triisopropylmethoxysilane. To the resulting reaction solution was added dropwise 40 ml of a saturated aqueous ammonium chloride solution to dissolve the magnesium salt in the latter. The organic layer was separated from the aqueous layer and the organic layer, was distilled to afford 28 g of triisopropylmethoxysilane as a fraction boiling at 85° C.-86° C./20 mm Hg. The yield was 73%.

Sources & evidence

ORD record
ord-cd27b084783d4666a9493817cf665dc8
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08008521B2

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes