Silane, (chloromethyl)triethoxy- → HCID 91654879, compound

HRID 1521811Notes

Reaction equation

HRID 1521811 reaction equation
Cl[CH2:2][Si:3]([O:10][CH2:11][CH3:12])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6].[Si:13]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])(Cl)Cl>C1COCC1>[Si:3]([CH2:2][Si:13]([CH2:2][Si:3]([O:4][CH2:5][CH3:6])([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])([O:10][CH2:11][CH3:12])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 84858Silane, (chloromethyl)triethoxy-HCID 138313Silane, dichlorodiethoxy-

Product 1

HCID 91654879HCID 91654879, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 molar equivalents of ClCH2Si(OEt)3, 2 molar equivalents of Mg (sanded ribbon), and molar 1 equivalent of SiCl2(OEt)2 were added in flask with THF (Na treated) under N2. The mixture was stirred at room temperature until Mg disappeared. THF was removed by distillation. Pentane was added to extract the intermediate and then filtered to separate solid. After distillation of pentane, >90% yield crude (EtO)3Si—CH2—Si(OEt)2-CH2—Si(OEt)3 was obtained. (EtO)3Si—CH2—Si(OEt)2-CH2—Si(OEt)3 was directly reduced without further purification by 3 molar equivalents (based on the amount of (EtO)3Si—CH2—Si(OEt)2-CH2—Si(OEt)3) of LiAlH4 in ether in ice bath under N2. The mixture was stirred for ˜6 hours at room temperature. The volatiles were separated from solid by-products and LiAlH4 by vacuum transfer, and ether was removed from the collected volatives by distillation using a 55° C. bath. The final distillation give pure trisilapentane (TSP) as 70% overall yield. The pure TSP was analysed by GC as shown in FIG. 2, which indicates no undesired by-products remain. TSP: 1H NMR (C6D6): δ 3.95 (p, 2H, SiH2), 3.67 (t, 6H, SiH3), −0.40 (m, 4H, CH2). MS, m/z: 120 [M+].

Workup

  1. customTHF was removed by distillation
  2. additionPentane was added
  3. extractionto extract the intermediate
  4. filtrationfiltered
  5. customto separate solid
  6. distillationAfter distillation of pentane

Sources & evidence

ORD record
ord-8bc63c999cc147cab51b9294fc42ec2f
Source dataset
uspto-grants-2015_07
Patent number
US09073952B1

Reaction notes

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