Water → HCID 22987177, compound

HRID 2304560Notes

Reaction equation

HRID 2304560 reaction equation
[CH2:1]([C:3]1([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([O:15]C)[CH:10]=2)OCCC[O:4]1)[CH3:2].[I-].[Na+].[Cl-].C[SiH](C)C.O>C(#N)C>[O:15]=[C:11]1[CH:10]=[C:9]([C:3](=[O:4])[CH2:1][CH3:2])[CH:14]=[CH:13][NH:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 108467324-(2-ethyl-1,3-dioxan-2-yl)-2-methoxypyridineHCID 131723440Tmsci

Product 1

HCID 22987177HCID 22987177, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(2-ethyl-1,3-dioxan-2-yl)-2-methoxypyridine (prepared according to the method described in the Patent Application PCT/FR96/00980, 57 g, 255 mmol) and sodium iodide (88 g, 580 mmol) in acetonitrile (1 l) is treated with trimethylsilane chloride (74 ml, 586 mmol), taken to reflux for 3 hours, then agitated at ambient temperature for 16 hours. The reaction medium is then treated with water (100 ml) and concentrated to dryness after elimination of the insolubles by filtration. The residue is taken up in ethyl acetate and washed successively with water and with an aqueous solution saturated in sodium chloride. The organic phase is dried, concentrated under reduced pressure, and the residue is taken up in diethyl ether in order to produce after filtration and drying 30 g (88%) of a white solid, m.p. 168° C.

Workup

  1. customprepared
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated to dryness after elimination of the insolubles
  4. filtrationby filtration
  5. washwashed successively with water and with an aqueous solution saturated in sodium chloride
  6. customThe organic phase is dried
  7. concentrationconcentrated under reduced pressure
  8. customto produce
  9. filtrationafter filtration
  10. dry with materialdrying 30 g (88%) of a white solid, m.p. 168° C.

Sources & evidence

ORD record
ord-2aa2302fcdb44fa1904cf5181edeabc2
Source dataset
uspto-grants-2002_08
Patent number
US06436951B1

Reaction notes

Loading…