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

HRID 1780064Notes

Reaction equation

[C:1](Cl)(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Cl: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]([Cl: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

Conditions

Temperature: 0 °C

Procedure

1.2 ml (7.1 mmol) of octanoyl chloride are added dropwise at 0° C. to 1.57 g (4.7 mmol) of 3-chloro-5-hydroxy-2-(4-octyloxyphenyl)pyridine in 20 ml of pyridine, and the mixture is stirred at 0° C. for 3 hours. The mixture is 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-chloro-2-(4-octyloxyphenyl)pyridin-5-yl octanoate. ##STR20##

Workup

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

Sources & evidence

ORD record: ord-e913b28c66154ff19bb37e4d2cfa4428
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05629428

Reaction notes

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