2,4,6-Trimethylpyridine → .alpha.-Hydroxy farnesyl phosphonic acid

Temperature

0 °C

To a stirred solution of dimethyl [1-hydroxy-(E,E)-3,7,11-trimethyl-2,6,10-dodecatrienyl]phosphonate (67 mg, 0.203 mmol) and 2,4,6-collidine (0.107 ml, 0.81 mmol)in dichloromethane (3 ml) under argon at 0° C., was added trimethylsilyl bromide (0.107 ml, 0.8 mmol) and the resulting mixture stirred at 0° C. for 30 min and then at r.t. for 5 hrs. 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 pH=3 by the addition of 1M HCl solution. The organic layer was separated, dried (MgSO4) and evaporated to afford a pale yellow solid. The-solid was washed with dichloromethane (2×5 ml) and the white solid filtered off and dried in vacuo to afford the title compound.

1. waitat r.t. for 5 hrs
2. customthe solvent evaporated in vacuo
3. dissolutionthe resulting white solid was dissolved in ethylacetate
4. additionwater and the pH was adjusted to pH=3 by the addition of 1M HCl solution
5. customThe organic layer was separated
6. dry with materialdried (MgSO4)
7. customevaporated
8. customto afford a pale yellow solid
9. washThe-solid was washed with dichloromethane (2×5 ml)
10. filtrationthe white solid filtered off
11. customdried in vacuo

ORD record

ord-63b3a3c305294643b57d5cde6aa6614b

Source dataset

uspto-grants-1994_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05362906