Triethylamine → HCID 19046971, compound

HRID 1780572Notes

Reaction equation

HRID 1780572 reaction equation
[F:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:12][CH:11]=2)[N:3]=1.[CH2:25]([CH:33]([CH2:36]O)[CH2:34][OH:35])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].S([O-])([O-])(=O)=O.[Na+].[Na+].C(N(CC)CC)C>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[F:1][C:2]1[C:7]([CH:8]2[O:35][CH2:34][CH:33]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:36][O:9]2)=[CH:6][CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:12][CH:11]=2)[N:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24436Sodium SulfateHCID 3160622-Octylpropane-1,3-diolHCID 19046983HCID 19046983, compound

Product 1

HCID 19046971HCID 19046971, compoundYield 41.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

2.20 g (6.68 mmol) of 2-fluoro-3-formyl-6-(4-octyloxyphenyl)pyridine, 1.26 g (6.68 mmol) of 2-octylpropane-1,3-diol, 0.02g (0.10mmol) of p-toluenesulfonic acid and 3.00 g of sodium sulfate are stirred in 100 ml of toluene at room temperature for 68 hours. 0.14 ml (1.00 mmol) of triethylamine is then added, sodium sulfate is filtered off, the filtrate is concentrated, and the residue is purified by chromatography (silica gel, 9:1 hexane/ethyl acetate) and by recrystallization from acetonitrile, giving 1.40 g of 2-fluoro-3-(5-octyl-1,3-dioxane-2-yl)-6-(4-octyloxyphenyl)pyridine. ##STR63##

Workup

  1. filtrationsodium sulfate is filtered off
  2. concentrationthe filtrate is concentrated
  3. customthe residue is purified by chromatography (silica gel, 9:1 hexane/ethyl acetate) and by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-9e14d2b82bf140c8b1d4d29f7c8e42bd
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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