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

HRID 2263548Notes

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 60 F) 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-e5f9118106a74d41b7976ee751ba1d72
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851634B2

Reaction notes

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