1-Octanol → 2-Fluoro-3-octyloxy-6-(6-octyloxynaphth-2-yl)pyridine

HRID 1780575Notes

Reaction equation

HRID 1780575 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:32][C:33]1[C:38]([OH:39])=[CH:37][CH:36]=[C:35]([C:40]2[CH:49]=[CH:48][C:47]3[C:42](=[CH:43][CH:44]=[C:45]([O:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[CH:46]=3)[CH:41]=2)[N:34]=1.[CH2:59](O)[CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66]>O1CCCC1>[F:32][C:33]1[C:38]([O:39][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])=[CH:37][CH:36]=[C:35]([C:40]2[CH:49]=[CH:48][C:47]3[C:42](=[CH:43][CH:44]=[C:45]([O:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[CH:46]=3)[CH:41]=2)[N:34]=1

Participants

6

Reactant 4

HCID 9571-OctanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 190469462-Fluoro-3-hydroxy-6-(6-octyloxynaphth-2-yl)pyridine

Product 1

HCID 190469662-Fluoro-3-octyloxy-6-(6-octyloxynaphth-2-yl)pyridineYield 88.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.06 g (6.11 mmol) of diethyl azodicarboxylate are added dropwise at 0° C. to 1.60 g (6.11 mmol) of triphenylphosphine in 50 ml of tetrahydrofuran, and the mixture is stirred at room temperature for 0.5 hour. 1.50 g (4.08 mmol) of 2-fluoro-3-hydroxy-6-(6-octyloxynaphth-2-yl)pyridine and 0.80 g (6.11 mmol) of 1-octanol are then added. After a reaction time of 1 hour at room temperature, the solvent is distilled off, and the residue is purified by chromatography (silica gel, 9:1 hexane/ethyl acetate) and by recrystallization from acetonitrile, giving 1.74 g of 2-fluoro-3-octyloxy-6-(6-octyloxynaphth-2-yl)pyridine. ##STR69##

Workup

  1. distillationAfter a reaction time of 1 hour at room temperature, the solvent is distilled off
  2. customthe residue is purified by chromatography (silica gel, 9:1 hexane/ethyl acetate) and by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-6d2f57702e2a4a66b9239d3c820f89ab
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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