Cyclohexanemethanol → HCID 22220026, compound

HRID 1794089Notes

Reaction equation

HRID 1794089 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[CH:11]1([CH2:17][OH:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[H-].[Na+]>>[CH:11]1([CH2:17][O:18][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 7507CyclohexanemethanolHCID 24758Sodium hydrideHCID 792226-Chloronicotinic acid

Product 1

HCID 22220026HCID 22220026, compound

Procedure

6-(Cyclohexylmethoxy)nicotinic acid was prepared from 6-chloronicotinic acid (0.50 g), cyclohexylmethanol (0.41 ml) and sodium hydride (60%, 0.32 g) according to the method described in Example 54 to give the product as a white solid (0.42 g, 56%): δH (400 MHz, DMSO-d6) 12.97 (1H, br), 8.70 (1H, d, J 2.5 Hz), 8.12 (1H, dd, J 8.5, 2.5 Hz), 6.88 (1H, d, J 8.5 Hz), 4.14 (2H, d, J 6 Hz), 1.81–1.60 (6H, m), 1.20 (3H, sept of triplets, J 12, 2.5 Hz) and 1.03 (2H, dq, J 11, 2.5 Hz); HPLC (XTERRA, 50/80,220 nm) 100% (1.47 min).

Sources & evidence

ORD record
ord-0823da4546d344d99f9df1cd20cfb610
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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