Trichlorosilane → HCID 88546035, compound

HRID 1522924Notes

Reaction equation

HRID 1522924 reaction equation
[C:1]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])(=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13].[SiH:21]([Cl:24])([Cl:23])[Cl:22]>>[Cl:22][Si:21]([Cl:24])([Cl:23])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:15][CH2:16][C:17]([F:18])([F:19])[F:20])=[O:14]

Participants

3

Reactant 2

HCID 24811TrichlorosilaneHCID 86660266HCID 86660266, compound

Product 1

HCID 88546035HCID 88546035, compound

Conditions

Temperature
80 °C

Procedure

In a heavy-walled tube equipped with a magnetic stir bar, ester (5) (1.18 g, 4.00 mmol, 1.0 equiv.) and H2PtCl6.6H2O (21 mg, 0.14 mmol, 1.0 mol. %) were loaded. The tube was transferred into a glovebox and HSiCl3 (0.82 mL, 8.04 mmol, 2.0 equiv.) was added to the solution. The tube was tightly fastened then removed from the glovebox. The resulting solution was stirred at 80° C. for 22 h behind a protecting shield. Purification was achieved by Kugelrohr distillation under high vacuum and provided 1.16 g (67%) of TTTA (6) as a colorless oil; bp=170-180° C. (0.15 Torr); 1H NMR (400 MHz, CDCl3) δ 4.45 (q, J=8.5 Hz, 2H), 2.41 (t, J=7.4 Hz, 2H), 1.72-1.55 (m, 4H), 1.45-1.22 (m, 18H); 13C NMR (100 MHz, CDCl3) δ 172.4, 123.3 (q, J=275.8 Hz), 60.3 (q, J=36.4 Hz), 33.9, 32.0, 29.8, 29.7, 29.6, 29.5, 29.4, 29.2, 29.1, 24.9, 24.5, 22.5.

Workup

  1. customIn a heavy-walled tube equipped with a magnetic stir bar
  2. customThe tube was transferred into a glovebox
  3. customThe tube was tightly fastened then removed from the glovebox
  4. customPurification
  5. distillationwas achieved by Kugelrohr distillation under high vacuum

Sources & evidence

ORD record
ord-1591e86c0ee94b57ad5872d292fa8705
Source dataset
uspto-grants-2015_07
Patent number
US09078956B2

Reaction notes

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