2,6-Lutidine → (3,5-Dichlorophenoxy)tris(propan-2-YL)silane

HRID 1043488

Reaction equation

HRID 1043488 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1.N1C(C)=CC=CC=1C.O([Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])S(C(F)(F)F)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([Cl:8])[CH:7]=1)[O:9][Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 115713,5-DichlorophenolHCID 2724529Triisopropylsilyl trifluoromethanesulfonate

Product 1

HCID 21594466(3,5-Dichlorophenoxy)tris(propan-2-YL)silaneYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3,5-dichloro-phenol (5.9 g, 36 mmol) in methylene chloride (50 mL) was added 2,6-lutidine (8.38 mL, 72.4 mmol) and triisopropylsilyl triflate (9.7 mL, 36 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 4 h. The reaction was quenched with 0.1 N HCl and diluted with ethyl acetate. The organic solution was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified with flash chromatography (5% ethyl acetate/hexanes) to give the desired product as a colorless oil (10.5 g, 91%). 1H NMR (400 MHz, CDCl3): δ 6.95 (t, J=1.8 Hz, 1H), 6.76 (d, J=1.8 Hz, 2H), 1.26 (m, 3H), 1.09 (d, J=7.0 Hz, 18H).

Workup

  1. customThe reaction was quenched with 0.1 N HCl
  2. additiondiluted with ethyl acetate
  3. washThe organic solution was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified with flash chromatography (5% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a337ba3aecfb4b9eb480244c81af7ac3
Source dataset
uspto-grants-2013_10
Patent number
US08563541B2

Linked notes

Loading…