Aluminium lithium hydride → [6-(3-Methyl-butoxy)-pyridin-3-yl]-methanol

HRID 1794087Notes

Reaction equation

HRID 1794087 reaction equation
[CH3:1][CH:2]([CH3:15])[CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](O)=[O:11])=[CH:8][N:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH3:1][CH:2]([CH3:15])[CH2:3][CH2:4][O:5][C:6]1[N:7]=[CH:8][C:9]([CH2:10][OH:11])=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 222199276-(3-Methylbutoxy)nicotinic acid

Product 1

HCID 22219862[6-(3-Methyl-butoxy)-pyridin-3-yl]-methanol

Procedure

[6-(3-Methyl-butoxy)-pyridin-3-yl]-methanol was prepared from 6-(3-methylbutoxy)nicotinic acid (0.24 g) and lithium aluminium hydride (0.5M, THF, 3.5 ml) according to the method described in Example 54 to give the product as a yellow oil (0.19 g, 86%): δH (400 MHz, CDCl3) 8.08 (1H, d, J 2.5 Hz), 7.59 (1H, dd, J 8.5, 2.5 Hz), 6.71 (1H, d, J 8.5 Hz), 4.60 (2H, s), 4.30 (2H, t, J 6.5 Hz), 1.81 (1H, nonet, J 6.7 Hz), 1.66 (3H, q, J 7 Hz) and 0.96 (6H, d, J 6.5 Hz); HPLC (XTERRA, 50/80, 235 nm) 86% (2.54 min).

Sources & evidence

ORD record
ord-7432c0f4d7864d8193bed8ef918e1e9c
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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