Water → HCID 86734390, compound

HRID 1414700Notes

Reaction equation

HRID 1414700 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[H-].[Na+].[CH2:11](Cl)/[CH:12]=[C:13](/[CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])\[CH3:14].O>CN(C=O)C>[CH3:14][C:13]([CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[CH:12][CH2:11][CH:2]([O:1][CH:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[CH2:11][CH:12]=[C:13]([CH3:14])[CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11474PiconolHCID 24758Sodium hydrideHCID 6372219Geranyl chloride

Product 1

HCID 86734390HCID 86734390, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 18.6 g. (0.20 moles) 2-hydroxymethylpyridine in dry DMF is added, in small portions, 8.8 g. of sodium hydride (60% in oil), and the mixture is stirred for one hour at 60° C. Then 34.6 g. (0.2 moles) geranylchloride is added and the reaction mixture is stirred overnight at 50°-60° C. 200 ml. of water is added to the reaction mixture, which then is extracted with ethyl ether. After separation the organic layer is washed with a 10% KOH solution and then with water until neutral. The extract is dried over anhydrous Na2SO4, and the solvent is removed in vacuo. The yield was 36.5 g. of the crude ether, which was purified on silica gel as described below. The actual compound have nD24 : 1.5048.

Workup

  1. additionTo a mixture of 18.6 g
  2. extractionthen is extracted with ethyl ether
  3. customAfter separation the organic layer
  4. washis washed with a 10% KOH solution
  5. dry with materialThe extract is dried over anhydrous Na2SO4
  6. customthe solvent is removed in vacuo
  7. customof the crude ether, which was purified on silica gel

Sources & evidence

ORD record
ord-5d0558773fb64dcea51e4f209f599f47
Source dataset
uspto-grants-1977_01
Patent number
US04002615

Reaction notes

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