Diethyl Ether → HCID 2737238, compound

HRID 361448Notes

Reaction equation

HRID 361448 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[B:13](OC)([O:16][CH3:17])[O:14][CH3:15].CCOCC>CCCCCC.C1COCC1>[CH3:15][O:14][B:13]([O:16][CH3:17])[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8470Trimethyl borateHCID 122863-BromopyridineHCID 178418339Butyllithium

Product 1

HCID 2737238HCID 2737238, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

n-Butyl lithium (31.3 ml of a 1.6M solution in hexane) was added to a stirred solution of 3-bromopyridine (4.8 ml) and trimethyl borate (6.2 ml) in dry THF (100 ml) at a rate such that the temperature did not exceed -65° C. The mixture was allowed to warm to ambient temperature over 16 hours and was filtered. The solid was washed with ether, combined with more solid obtained from the filtrate and rewashed with ether to give dimethoxy-(3-pyridyl)borane (3.5 g) as a solid, 1H NMR (CD3OD): 3.4 (s, 6 H), 7.2 (m, 1 H), 7.9 (m, 1 H), 8.2 (dd, 1 H), 8.6 (s, 1 H); mass spectrum (+ve CI): 152 (M+H)+.

Workup

  1. customdid not exceed -65° C
  2. filtrationwas filtered
  3. washThe solid was washed with ether
  4. customobtained from the filtrate

Sources & evidence

ORD record
ord-d88025a540e94f69907f66daff9381e4
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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