Tetrahydrofuran → HCID 18918573, compound

HRID 864865Notes

Reaction equation

HRID 864865 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH:9]([CH3:15])C(OCC)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:23]1CCC[CH2:24]1>>[CH3:16][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH2:9][CH2:15][CH2:24][OH:23]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 18918255HCID 18918255, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18918573HCID 18918573, compound

Procedure

To a stirred solution of the product of step (iv) (2.6 g) in tetrahydrofuran (100 ml) was added lithium aluminium hydride (1.2 g) and the resulting suspension stirred for 4 hours at ambient temperature. Excess reducing agent was destroyed by the sequential addition of ethyl acetate, water, and conc. HCl. The mixture was then basified and extracted sequentially with ethyl acetate and dichloromethane. The organic extracts were combined, dried (PS paper and MgSO4) and evaporated to yield 4-dimethylamino-3-(3-hydroxypropyl)pyridine as a pale yellow oil (2.2 g), essentially pure by Tlc NMR (d6DMSO): δ1.6-1.8 (2H,m); 2.65 (2H,t); 2.8 (6H,s); 3.5 (2H,t); 4.5 (1H,br.s); 6.7 (2H,d); 8.2 (2H,d); m/e 181 (M+H)+.

Workup

  1. customwas destroyed by the sequential addition of ethyl acetate, water, and conc. HCl
  2. extractionextracted sequentially with ethyl acetate and dichloromethane
  3. dry with materialdried (PS paper and MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-473f2c7d61654275b33944075cd9a993
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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