Iodine → 3-(3-Iodo-2-propynyloxy)pyridine
Reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)[C:2]#[CH:3].[OH-].[Na+].[I:13]I.O>CO>[I:13][C:3]#[C:2][CH2:1][O:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
In 300 ml methanol was dissolved 39.0 g (0.27 mole) 3-(2-propynyloxy)pyridine. This solution was cooled to 0° C. and 54.0 g (1.35 moles) sodium hydroxide was added slowly while maintaining the temperature at 0°-5° C. Iodine (82.0 g, 0.32 mole) was added portionwise followed by the addition of 400 ml methanol. After stirring for 2 hours at room temperature, the reaction mixture was poured into cold water. The resulting precipitate was filtered and dried. This crude product was recrystallized from 350 ml methanol and 75 ml toluene to give 60.0 g (86% yield) 3-(3-iodo-2-propynyloxy)pyridine, mp 130° C. with decomposition.
Workup
- temperaturewhile maintaining the temperature at 0°-5° C
- filtrationThe resulting precipitate was filtered
- customdried
- customThis crude product was recrystallized from 350 ml methanol and 75 ml toluene
Sources & evidence
- ORD record
- ord-dd81a9bcdf6d44b3a5a6c2e17603467e
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04220577
Reaction notes
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