Sodium hydride → HCID 20271453, compound

HRID 485094Notes

Reaction equation

HRID 485094 reaction equation
[OH:1][C:2]1[C:3]([CH2:9][CH2:10][CH2:11][C:12]#[N:13])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[H-].[Na+].[CH2:16](I)[CH2:17][CH3:18]>CS(C)=O>[CH2:16]([O:1][C:2]1[C:3]([CH2:9][CH2:10][CH2:11][C:12]#[N:13])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1)[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 20271449HCID 20271449, compound

Product 1

HCID 20271453HCID 20271453, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 3-hydroxy-2-(3-cyanopropyl)-5-methylpyridine from Example 3(a) (1.5 g), in dimethyl sulphoxide (11 ml) was first treated with sodium hydride (0.2 g) and then with n-propyl iodide in dimethyl sulphoxide (3 ml) at 17°-20° C. After stirring for four hours at room temperature, the solvent was removed in vacuo and the residue partitioned between chloroform and water, the chloroform extract was evaporated to dryness to give 3-n-propyloxy-2-(3-cyanopropyl)-5-methylpyridine (1.79 g) N.M.R. (CDCl3), assignment, δ(p.p.m.), multiplicity; O(CH2)2CH3, 1.07, t; OCH2CH2CH3, 1.86, m; CH2CH2CN, 2.12, m; CH2CN, 2.40, m; 5--CH3, 2.30, s; CH2 (CH2)2CN, 3.94, m; OCH2, 3.91, t; 4--H pyridyl, 6.96, m; 6--H pyridyl, 7.91, m;

Workup

  1. customat 17°-20° C
  2. customthe solvent was removed in vacuo
  3. customthe residue partitioned between chloroform and water
  4. extractionthe chloroform extract
  5. customwas evaporated to dryness

Sources & evidence

ORD record
ord-9fbd76ef221f4e7a86e52f8f99f068d3
Source dataset
uspto-grants-1985_08
Patent number
US04535163

Reaction notes

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