2,4,6-Trimethylpyridine → HCID 15235907, compound

HRID 2379545Notes

Reaction equation

HRID 2379545 reaction equation
[C:1]([NH:4][CH:5](/[CH:13]=[C:14](\[CH3:26])/[CH2:15][CH2:16]/[CH:17]=[C:18](\[CH3:25])/[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])[CH2:6][P:7](=[O:12])([O:10]C)[O:8]C)(=[O:3])[CH3:2].N1C(C)=CC(C)=CC=1C.C[Si](Br)(C)C>ClCCl.C1(C)C=CC=CC=1.[OH-].[NH4+]>[C:1]([NH:4][CH:5](/[CH:13]=[C:14](\[CH3:26])/[CH2:15][CH2:16]/[CH:17]=[C:18](\[CH3:25])/[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])[CH2:6][P:7](=[O:8])([OH:10])[OH:12])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 76113BromotrimethylsilaneHCID 21756374HCID 21756374, compound

Product 1

HCID 15235907HCID 15235907, compound

Reagents, catalysts & solvents 3

HCID 14923Ammonium HydroxideCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of dimethyl [2-acetamido-(E,E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]phosphonate (39 mg, 0.101 mmol) and 2,4,6-collidine (0.054 ml, 0.404 mmol) in dichloromethane (2.5 ml) under argon at 0° C., was added trimethylsilyl bromide (0.054 ml, 0.404 mmol) and the resulting mixture stirred at 0° C. for 30 min and then at r.t. for 5 hr. The resulting white suspension was diluted with toluene (10 ml) and the solvent evaporated in vacuo. The resulting white solide was dissolved in ethylacetate and water and the pH was adjusted to 3 by the addition of 1M HCl solution. The organic layer was separated, dried (Na2SO4) and evaporated to afford a clear oil, which was dissolved in hexanes and treated with 10 drops of ammonium hydroxide, the precipitate was removed by filtration and dried in vacuo to afford the title compound as an off white solid.

Workup

  1. waitat r.t. for 5 hr
  2. customthe solvent evaporated in vacuo
  3. dissolutionThe resulting white solide was dissolved in ethylacetate
  4. additionwater and the pH was adjusted to 3 by the addition of 1M HCl solution
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customto afford a clear oil, which
  9. customthe precipitate was removed by filtration
  10. customdried in vacuo

Sources & evidence

ORD record
ord-a08ec19916d44daebd9e61c04ce57eaf
Source dataset
uspto-grants-1994_11
Patent number
US05362906

Reaction notes

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