Trichlorosilane → Trichloro[3-(thiophen-2-yl)propyl]silane

HRID 444656Notes

Reaction equation

HRID 444656 reaction equation
[CH2:1]([C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)[CH:2]=[CH2:3].[Cl:9][SiH:10]([Cl:12])[Cl:11]>[Pt].C1(C)C=CC=CC=1>[Cl:9][Si:10]([Cl:12])([Cl:11])[CH2:3][CH2:2][CH2:1][C:4]1[S:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 24811TrichlorosilaneHCID 6423302-allylthiophene

Product 1

HCID 66863562Trichloro[3-(thiophen-2-yl)propyl]silane

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

2-Allylthiophene (25 g), 13 g of anhydrous toluene (13 g), and 250 mg of Platinum Catalyst were combined under nitrogen in a three-neck flask equipped with a reflux condenser and a dropping funnel. Then, 30 g of trichlorosilane was added drop-wise to the mixture. Upon completion of the addition, the mixture was heated to 60° C. and maintained at that temperature for 2 h. Then, the mixture was distilled at 150° C. and 0.02 ton to give 2-(3-trichlorosilylpropyl)thiophene as a colorless liquid: 1H NMR (CDCl3) δ 7.16 (dd, 1H, J=5.1, 0.9 Hz); 6.95 (dd, 1H, J=4.8, 3.3 Hz); 6.83 (m, 1H); 2.96 (t, 2H, J=7.2 Hz); 1.98 (m, 2H); 1.46 (m, 2H).

Workup

  1. customequipped with a reflux condenser and a dropping funnel
  2. additionUpon completion of the addition
  3. temperaturemaintained at that temperature for 2 h
  4. distillationThen, the mixture was distilled at 150° C.

Sources & evidence

ORD record
ord-ab09b03f892647d0bd305f5e43c55d6d
Source dataset
uspto-grants-2013_07
Patent number
US08475937B2

Reaction notes

Loading…