5-Ethyl-2-methylpyridine → HCID 178419175, compound

HRID 425268Notes

Reaction equation

HRID 425268 reaction equation
[B:1]#B.[CH2:3]([C:5]1[CH:6]=[CH:7][C:8]([CH3:11])=[N:9][CH:10]=1)[CH3:4]>C1(C)C=CC=CC=1>[BH3:1].[CH2:3]([C:5]1[CH:6]=[CH:7][C:8]([CH3:11])=[N:9][CH:10]=1)[CH3:4]

Participants

4

Reactant 2

HCID 77285-Ethyl-2-methylpyridineHCID 6328200Diboron

Product 1

HCID 178419175HCID 178419175, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Diborane (1.4 g) was added to a solution of 5-ethyl-2-methylpyridine (12.1 g) in toluene (50 ml) to form a 2M solution of 5-ethyl-2-methylpyridine borane. The temperature of the solution rose 4 degrees during the borane addition. The 11B NMR spectrum showed a quartet at δ=−13.3 ppm (1J(11B1H)=98 Hz). The DSC of the solution had an onset at 212° C. and an energy release of −152 J/g. The solvent was removed under vacuum from 30 ml (27.4 g) of the solution to leave a liquid product (6.4 g, 90% yield). 1H NMR indicated a trace of toluene (<0.5%) remaining.

Sources & evidence

ORD record
ord-d1ef1d1a50424e87b9bcbd2542564f9e
Source dataset
uspto-grants-2012_01
Patent number
US08106200B2

Reaction notes

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