Octanoyl chloride → 3-Fluoro-2-(4-octyloxyphenyl)pyridin-5-yl octanoate

HRID 1757357Notes

Reaction equation

HRID 1757357 reaction equation
[C:1](Cl)(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[F:11][C:12]1[C:13]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:21][CH:20]=2)=[N:14][CH:15]=[C:16]([OH:18])[CH:17]=1>N1C=CC=CC=1>[C:1]([O:18][C:16]1[CH:17]=[C:12]([F:11])[C:13]([C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:23][CH:24]=2)=[N:14][CH:15]=1)(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 8124Octanoyl chlorideHCID 19387549HCID 19387549, compound

Product 1

HCID 542251573-Fluoro-2-(4-octyloxyphenyl)pyridin-5-yl octanoateYield 64.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.2 ml (7.1 mmol) of octanoyl chloride are added dropwise at O° C. to 1.5 g (4.7 mmol) of 3-fluoro-5-hydroxy-2-(4octyloxyphenyl)pyridine in 20 ml of pyridine and the mixture is stirred at 0° C. for 3 hours, subsequently poured into ice-water and filtered and the residue is purified by chromatography (silica gel/hexane: ethyl acetate 9:1) and by recrystallization from acetonitrile, giving 1.34 g of 3-fluoro-2-(4-octyloxyphenyl)pyridin-5-yl octanoate. ##STR20##

Workup

  1. filtrationfiltered
  2. customthe residue is purified by chromatography (silica gel/hexane: ethyl acetate 9:1) and by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-d646b0778e3a4653bac5a7c4844efc88
Source dataset
uspto-grants-1995_08
Patent number
US05445763

Reaction notes

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