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

HRID 1780556Notes

Reaction equation

HRID 1780556 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]([C:46]3[CH:51]=[CH:50][C:49]([O:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])=[CH:48][CH:47]=3)=[CH:42][CH:41]=2)[N:34]=1.[CH2:61](O)[CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH3:68]>O1CCCC1>[F:32][C:33]1[C:38]([O:39][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH3:68])=[CH:37][CH:36]=[C:35]([C:40]2[CH:41]=[CH:42][C:43]([C:46]3[CH:51]=[CH:50][C:49]([O:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])=[CH:48][CH:47]=3)=[CH:44][CH:45]=2)[N:34]=1

Participants

6

Reactant 4

HCID 9571-OctanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 190469362-Fluoro-3-hydroxy-6-[4-(4-octyloxyphenyl)phenyl]pyridine

Product 1

HCID 190469792-Fluoro-3-octyloxy-6-[4-(4-octyloxyphenyl)phenyl]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.02 ml (6.45 mmol) of diethyl azodicarboxylate are added dropwise at 0° C. to 1.70 g (6.45 mmol) of triphenylphosphine in 100 ml of tetrahydrofuran and the mixture is stirred at room temperature for 30 minutes. 1.70 g (4.30 mmol) of 2-fluoro-3-hydroxy-6-[4-(4-octyloxyphenyl)phenyl]pyridine and 0.56 g (4.30 mm 1-octanol are then added. After a reaction time of 18 hours, the precipitated product is filtered off and purified by chromatography (silica gel, dichloromethane) and by recrystallization from acetonitrile, giving 1.13 g of 2-fluoro-3-octyloxy-6-[4-(4-octyloxyphenyl)phenyl]pyridine. ##STR26##

Workup

  1. filtrationAfter a reaction time of 18 hours, the precipitated product is filtered off
  2. custompurified by chromatography (silica gel, dichloromethane) and by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-3e56eb77b82a4462a5a09d39038fad5f
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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