2-Fluoropyridine → HCID 57804716, compound

HRID 2103957Notes

Reaction equation

HRID 2103957 reaction equation
[SH:1][CH2:2][CH2:3][CH2:4][Si:5]([CH3:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8].[CH2:13](O[K])C.[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1>C(O)C>[CH2:7]([O:6][Si:5]([O:9][CH2:10][CH3:11])([CH3:12])[CH2:4][CH2:3][CH2:2][S:1][CH2:13][C:22]1[CH:21]=[CH:20][N:19]=[C:18]([F:17])[CH:23]=1)[CH3:8]

Participants

5

Reactant 3

HCID 97462-FluoropyridineHCID 185420023-MercaptopropylmethyldiethoxysilaneHCID 178473702HCID 178473702, compound

Product 1

HCID 57804716HCID 57804716, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

10 mmole of 3-mercaptopropylmethyldiethoxysilane was dissolved in 10 ml ethanol, then 10 mmole EtOK was added, and stirred for 5 minutes. 10 mmole of 2-fluoropyridine in 10 ml ethanol was added to the solution, and stirred for 30 minutes. The white precipitate was removed by filtration, the solvent in the filtrate was removed in vacuum. The product was purified with a short Si gel column. The solvent was 1:3 ethyl acetate:hexane by volume. 1H NMR (CD3Cl): δ(ppm) 0.03 (3H, s), 0.60 (2H, m), 1.15 (6H, m), 1.55 (2H, m), 2.40 (2H, m), 3.65 (4H, m), 6.85 (1H, s), 7.09 (1H, d, JH-H=5.02), 8.08 (1H, d, JH-H=5.02. Yield: 78%.

Workup

  1. stirringstirred for 30 minutes
  2. customThe white precipitate was removed by filtration
  3. customthe solvent in the filtrate was removed in vacuum
  4. customThe product was purified with a short Si gel column

Sources & evidence

ORD record
ord-e59145c6bb884a9995c86fe574ab20fb
Source dataset
uspto-grants-2009_08
Patent number
US07576165B2

Reaction notes

Loading…