1-Octanol → 2-Fluoro-3-(octyloxy)-6-[4-(octyloxy)phenyl]pyridine

HRID 1780549Notes

Reaction equation

HRID 1780549 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:45]=[CH:44][C:43]([O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])=[CH:42][CH:41]=2)[N:34]=1.[CH2:55](O)[CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62]>O1CCCC1>[F:32][C:33]1[C:38]([O:39][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])=[CH:37][CH:36]=[C:35]([C:40]2[CH:45]=[CH:44][C:43]([O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])=[CH:42][CH:41]=2)[N:34]=1

Participants

6

Reactant 4

HCID 9571-OctanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 190469612-(4-Octyloxyphenyl)-5-hydroxy-6-fluoropyridine

Product 1

HCID 190469592-Fluoro-3-(octyloxy)-6-[4-(octyloxy)phenyl]pyridineYield 41.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.00 g (11.5 mmol) of diethyl azodicarboxylate are added dropwise at 0° C. to 3.00 g (11.5 mmol) of triphenylphosphine in 50 ml of tetrahydrofuran, and the mixture is stirred at room temperature for 30 minutes. 2.42 g (7.7 mmol) of 2-fluoro-3-hydroxy-6-(4-octyloxyphenyl)pyridine and 1.00 g (7.7 mmol) of 1-octanol are then added. After a reaction time of 18 hours at room temperature, the solvent is distilled off, and the residue is purified by chromatography (silica gel, 95:5 hexane/ethyl acetate). Recrystallization from acetonitrile gives 1.38 g of 2-fluoro-3-octyloxy-6-(4-octyloxyphenyl)pyridine. ##STR19##

Workup

  1. distillationAfter a reaction time of 18 hours at room temperature, the solvent is distilled off
  2. customthe residue is purified by chromatography (silica gel, 95:5 hexane/ethyl acetate)
  3. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-6f97ea7a9b954c339563f835fbddce8e
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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