Water → 2-Iodo-5-methoxy-4-(3-methoxy-propoxy)pyridine

HRID 252364Notes

Reaction equation

I[C:2]1[C:7]([O:8][CH3:9])=[C:6]([O: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]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[C:7]([O:8][CH3:9])=[CH:2][N:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

2 mmol of 2,6-diiodo-3-methoxy-4-(3-methoxy-propoxy)-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 allowed to reach 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

customto reach room temperature
extractionfollowed by extraction with tert-butyl methyl ether (3×)
dry with materialThe combined organic layers are dried over sodium sulphate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-c36b99f0a4294a26b3feed4855864fb8
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868036B2

Reaction notes

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