Ethyltriethoxysilane → HCID 23303874, compound

HRID 1953177Notes

Reaction equation

C([Mg]Cl)(C)C.[CH:6]1([NH2:12])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[CH2:13]([Si:15](OCC)([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])[CH3:14]>O1CCCC1>[CH2:13]([Si:15]([NH:12][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])[CH3:14]

Participants

Conditions

Temperature: 70 °C

Procedure

Following the same general procedure described in Example 1, a 500 ml, four-necked flask fitted with a pressure equalizing funnel was charged with 0.5 mol of isopropylmagnesium chloride in 250 ml of tetrahydrofuran. Cyclohexylamine, 0.55 mol (52 g), was added over 30 minutes via a pressure equalizing funnel. The contents were refluxed for 15 minutes to complete the evolution of gas. Ethyltriethoxysilane, 0.5 mol (96 g) was added via the pressure equalizing funnel. The contents were refluxed at a pot temperature of 70° C. for two hours. Ethyl(cyclohexylamino)diethoxysilane was filtered under nitrogen atmosphere from the magnesium ethoxychloride. The filter cake was washed with ether (2×100 ml) to obtain the residual product. The solvent was removed via rotary evaporation. The residue was distilled under vacuum to yield 102 g of ethyl(cyclohexylamino)diethoxysilane as a colorless oil (purity>98%); bp 68° C./0.5 mm. The total yield was 83% of theoretical.

Workup

customa 500 ml, four-necked flask fitted with a pressure
temperatureThe contents were refluxed for 15 minutes
filtrationEthyl(cyclohexylamino)diethoxysilane was filtered under nitrogen atmosphere from the magnesium ethoxychloride
washThe filter cake was washed with ether (2×100 ml)
customto obtain the residual product
customThe solvent was removed via rotary evaporation
distillationThe residue was distilled under vacuum

Sources & evidence

ORD record: ord-488e53b2f0eb434085e6e31ba38430ba
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06114558

Reaction notes

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