Octanoyl chloride → HCID 53938776, compound

HRID 1780550Notes

Reaction equation

HRID 1780550 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:17]([OH:18])=[CH:16][CH:15]=[C:14]([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:13]=1>N1C=CC=CC=1>[C:1]([O:18][C:17]1[C:12]([F:11])=[N:13][C:14]([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)=[CH:15][CH:16]=1)(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 8124Octanoyl chlorideHCID 190469612-(4-Octyloxyphenyl)-5-hydroxy-6-fluoropyridine

Product 1

HCID 53938776HCID 53938776, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

1.2 ml (7.1 mmol) of octanoyl chloride are added dropwise at 0° C. to 1.5 g (4.7 mmol) of 2-fluoro-3-hydroxy-6-(4-octyloxyphenyl)pyridine (prepared as described in Example 3) in 20 ml of pyridine, and the mixture is stirred at 0° C. for 3 hours. It is then poured onto ice water, filtered off and the residue is purified by chromatography (silica gel, 9:1 hexane/ethyl acetate) and by recrystallization from acetonitrile, giving 1.34 g of 2-fluoro-6-(4-octyloxyphenyl)pyridine-3-yl octanoate. ##STR20##

Workup

  1. additionIt is then poured onto ice water
  2. filtrationfiltered off
  3. customthe residue is purified by chromatography (silica gel, 9:1 hexane/ethyl acetate) and by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-c8653cbbd2374cea95806004b2d8e461
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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