1-Octanol → 3-Chloro-5-octyloxy-2-(4-octyloxyphenyl)pyridine
Reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:32][C:33]1[C:34]([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:35][CH:36]=[C:37]([OH:39])[CH:38]=1.[CH2:55](O)[CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62]>O1CCCC1>[Cl:32][C:33]1[C:34]([C:40]2[CH:41]=[CH:42][C:43]([O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])=[CH:44][CH:45]=2)=[N:35][CH:36]=[C:37]([O:39][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])[CH:38]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
0.6 ml (3.8 mmol) of diethyl azodicarboxylate is added dropwise at 0° C. to 1.00 g (3.80 mmol) of triphenylphosphine in 15 ml of tetrahydrofuran, and the mixture is stirred at room temperature for 30 minutes. 0.78 g (2.5 mmol) of 3-chloro-5-hydroxy-2-(4-octyloxyphenyl)-pyridine and 0.6 ml (3.8 mmol) of 1-octanol are subsequently added. After a reaction time of 18 hours at room temperature, the solvent is removed by distillation and the residue is purified by chromatography (silica gel, dichloromethane). Recrystallization from acetonitrile gives 0.63 g of 3-chloro-5-octyloxy-2-(4-octyloxyphenyl)pyridine. ##STR19## The compound has the phase sequence: X 32.2 (6.5) N 17 I.
Workup
- customAfter a reaction time of 18 hours at room temperature, the solvent is removed by distillation
- customthe residue is purified by chromatography (silica gel, dichloromethane)
- customRecrystallization from acetonitrile
Sources & evidence
- ORD record
- ord-471f4d88f286432680ea7bb7f65d333a
- Source dataset
- uspto-grants-1997_05
- Patent number
- US05629428
Reaction notes
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