Ethyl 2-n-propylpyridine-3-carboxylate → Hydroxymethyl-2-n-propylpyridin

HRID 1422108Notes

Reaction equation

HRID 1422108 reaction equation
[CH2:1]([C:4]1[C:9]([C:10](OCC)=[O:11])=[CH:8][CH:7]=[CH:6][N:5]=1)[CH2:2][CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[OH:11][CH2:10][C:9]1[C:4]([CH2:1][CH2:2][CH3:3])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 18706942Ethyl 2-n-propylpyridine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 18707030Hydroxymethyl-2-n-propylpyridinYield 90%

Procedure

Ethyl 2-n-propylpyridine-3-carboxylate was reduced with lithium aluminum hydride by the general synthetic principle outlined in example 1, step 4, to afford 3 hydroxymethyl-2-n-propylpyridin as a yellow oil in 90% yield. 1H--NMR (CDCl3, 200 MHz) δ: 0.98 (t, 3 H); 1.72 (sextet, 2 H); 2.75 (t, 2 H); 3.35 (br s, 1 H); 4.74 (s, 2 H); 7.12 (dd, 1 H); 7.74 (dd, 1 H); 8.39 (dd, 1 H).

Sources & evidence

ORD record
ord-2dc2e6711def4f74a95f0885e916d2e2
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

Loading…