Water → HCID 86071606, compound

HRID 252366Notes

Reaction equation

HRID 252366 reaction equation
I[C:2]1[C:7]([O:8][CH3:9])=[C:6]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:5]=[C:4]([I:16])[N:3]=1.C([Li])CCC.O.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[I:16][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[C:7]([O:8][CH3:9])=[CH:2][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 23149473HCID 23149473, compoundHCID 178418339Butyllithium

Product 1

HCID 86071606HCID 86071606, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

2 mmol of 2,6-diiodo-3-methoxy-4-(4-methoxy-butyl)-pyridine are added to a solution of 4 mmol n-butyllithium in 1.6 ml hexane and 10 ml tetrahydrofuran at −78° C. under an argon atmosphere. The reaction mixture is stirred at −78° C. for 15 minutes. 2 mmol of water are introduced and the reaction mixture is warmed to room temperature. 10% Aqueous ammonium chloride solution is added to the mixture followed by extraction with tert-butyl methyl ether (3×). The combined organic layers are dried over sodium sulphate, filtered and concentrated. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) and identified based on its Rf value.

Workup

  1. temperaturethe reaction mixture is warmed to room temperature
  2. extractionfollowed by extraction with tert-butyl methyl ether (3×)
  3. dry with materialThe combined organic layers are dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1b676e359b6e4eac922bbbf6966ffd40
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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