1-Bromopropane → 2-[4-(5-[Propyloxy]-1-pentyl)phenyl]-5-hydroxypyridine

HRID 1728275Notes

Reaction equation

HRID 1728275 reaction equation
C[Si](C)(C)[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21])=[CH:12][CH:11]=2)=[N:8][CH:9]=1.[H-].[Na+].Br[CH2:27][CH2:28][CH3:29]>O1CCCC1>[OH:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:27][CH2:28][CH3:29])=[CH:12][CH:11]=2)=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 19017137HCID 19017137, compound

Product 1

HCID 190170922-[4-(5-[Propyloxy]-1-pentyl)phenyl]-5-hydroxypyridineYield 77.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.1 g of 5-trimethylsilyloxy-2-(4-[5-hydroxy-1-pentyl]phenyl)pyridine, 0.7 g of sodium hydride (60-65 wt. %), 2.5 g of 1-bromopropane and 100 ml of tetrahydrofuran were reacted analogously to Example 1(f) to give 3.6 g of 5-hydroxy-2-(4-[5-(propyloxy)-1-pentyl]phenyl)pyridine.

Sources & evidence

ORD record
ord-b127a732fd8541039c9eb3adb7943cfb
Source dataset
uspto-grants-1994_07
Patent number
US05326497

Reaction notes

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