Reaction equation
[Li+].CCC[CH2-].Br[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.[CH2:13]([B:15]([CH2:18][CH3:19])OC)[CH3:14].C(OCC)(=O)C>CCOCC.[Cl-].[Na+].O>[CH2:13]([B:15]([CH2:18][CH3:19])[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)[CH3:14]Participants
Conditions
- Temperature
- -40 °C
Procedure
N-Butyllithium (1.6M in hexanes, 20 ml) was added to dry ether (100 ml) and cooled to −40° C. under nitrogen. The solution was stirred and a solution of 4-Bromopyridine (32 mmols) dissolved in dry ether was added drop wise. The ethereal solution was stirred for 30 minutes at −40° C. then cooled to −70° C. Diethyl methoxy borane (4.6 ml) dissolved in dry ether (50 ml) was added drop wise and the mixture was allowed to warm to room temperature over night. Ethyl acetate (100 ml) and brine (70 ml) were added to the resulting brown solution and the organic layer was separated. This was dried over magnesium sulfate, filtered and evaporated to yield a brown tar. The product was purified by column chromatography on silica eluted with toluene to yield (0.94 g, 6.4 mmols) of Diethyl (4-pyridyl borane) (I) as a white solid.
Workup
- additionwas added drop wise
- stirringThe ethereal solution was stirred for 30 minutes at −40° C.
- temperaturethen cooled to −70° C
- additionwas added drop wise
- temperatureto warm to room temperature over night
- customthe organic layer was separated
- dry with materialThis was dried over magnesium sulfate
- filtrationfiltered
- customevaporated
- customto yield a brown tar
- customThe product was purified by column chromatography on silica
- washeluted with toluene
Sources & evidence
- ORD record
- ord-5f209412a0e34e0d8cf7cf77a42a0b89
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08647827B2
Linked notes
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