1-Octanol → HCID 178443705, compound

HRID 1780569Notes

Reaction equation

HRID 1780569 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@H:46]3[CH2:51][CH2:50][C@H:49]([CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[CH2:48][CH2:47]3)=[CH:42][CH:41]=2)[N:34]=1.[CH2:57](O)[CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64]>O1CCCC1>[F:32][C:33]1[C:38]([O:39][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])=[CH:37][CH:36]=[C:35]([C:40]2[CH:45]=[CH:44][C:43]([C@H:46]3[CH2:51][CH2:50][C@H:49]([CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[CH2:48][CH2:47]3)=[CH:42][CH:41]=2)[N:34]=1

Participants

6

Reactant 4

HCID 9571-OctanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178444290HCID 178444290, compound

Product 1

HCID 178443705HCID 178443705, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.26 g (1.50 mmol) of diethyl azodicarboxylate is added dropwise at 0° C. to 0.39 g (1.50 mmol) of triphenylphosphine in 10 ml of tetrahydrofuran, and the mixture is stirred at room temperature for 30 minutes. 0.31 g (0.91 mmol) of 2-fluoro-3-hydroxy-6-[4-(trans-4-pentylcyclohexyl)phenyl]pyridine and 0.19 g (1.50 mmol) of 1-octanol are then added. After a reaction time of 2hours 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 0.20 g of 2-fluoro-3-octyloxy-6-[4-(trans-4-pentylcyclohexyl)phenyl]pyridine. ##STR52##

Workup

  1. distillationAfter a reaction time of 2hours 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-f884640e437c4aaba7d430b3beb6dbeb
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

Loading…