2,4,6-Trimethylpyridine → HCID 18957432, compound

HRID 2379539Notes

Reaction equation

HRID 2379539 reaction equation
C[O:2][P:3]([CH:7]([OH:24])[CH2:8][CH2:9]/[CH:10]=[C:11](\[CH3:23])/[CH2:12][CH2:13]/[CH:14]=[C:15](\[CH3:22])/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])(=[O:6])[O:4]C.N1C(C)=CC(C)=CC=1C.C[Si](Br)(C)C>ClCCl.C1(C)C=CC=CC=1>[OH:24][CH:7]([P:3](=[O:2])([OH:6])[OH:4])[CH2:8][CH2:9]/[CH:10]=[C:11](\[CH3:23])/[CH2:12][CH2:13]/[CH:14]=[C:15](\[CH3:22])/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:20])[CH3:21]

Participants

6

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 76113BromotrimethylsilaneHCID 21756367HCID 21756367, compound

Product 1

HCID 18957432HCID 18957432, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of dimethyl[1-hydroxy-(E,E)-5,9,13-trimethyl-4,8,12-tetradecatrienyl]phosphonate (98 mg, 0.253 mmol) and 2,4,6-collidine (0.134 ml, 1.014 mmol) in dichloromethane (3 ml) under arson at 0° C., was added trimethylsilyl bromide (0.134 ml, 1.013 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 solid 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 glassy residue. The solid was washed with acetonitrile (2×5 ml) and the white solid filtered off and dried in vacuo to afford the title compound.

Workup

  1. waitat r.t. for 5 hr
  2. customthe solvent evaporated in vacuo
  3. dissolutionthe resulting white solid 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 glassy residue
  9. washThe solid was washed with acetonitrile (2×5 ml)
  10. filtrationthe white solid filtered off
  11. customdried in vacuo

Sources & evidence

ORD record
ord-7f67b3e5a05b400eb1bc656baf5acdf4
Source dataset
uspto-grants-1994_11
Patent number
US05362906

Reaction notes

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