2-Bromopyridine → HCID 15475347, compound

HRID 566243Notes

Reaction equation

HRID 566243 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[O:19][CH2:20][CH:21]1[CH2:24]C[O:22]1.B(F)(F)F.CCOCC.C(=O)([O-])O.[Na+]>C(OCC)C.CCCCCC>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH2:24][CH:21]([OH:22])[CH2:20][O:19][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][O:13]1

Participants

8

Reactant 5

HCID 79732-BromopyridineHCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 15475346HCID 15475346, compoundHCID 178418339Butyllithium

Product 1

HCID 15475347HCID 15475347, compoundYield 27.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

2-Bromopyridine (9.48 g) was dissolved in diethyl ether (100 ml). To the solution was added dropwise, at −70° C., n-butyl lithium (a 1.6M hexane solution, 37.5 ml). The mixture was stirred for 5 minutes at the same temperature. To the reaction mixture was added a solution of 2-(2-tetrahydropyranyloxymethyl)oxetane (3.13 g) in diethyl ether (10 ml). To the mixture was added boron trifluoride ethyl etherate (7.6 ml), followed by stirring for 20 minutes at the same temperature. To the reaction mixture was added an aqueous solution of sodium hydrogencarbonate (60 ml), followed by extraction with ethyl acetate four times. The organic layer was dried over anhydrous sodium sulfate, which was then concentrated. The concentrate was purified by means of a column chromatography (carrier: silica gel, 200 g, developing solvent: ethyl acetate-hexane, 4:1) to give the title compound (1.19 g).

Workup

  1. additionTo the solution was added dropwise, at −70° C.
  2. stirringby stirring for 20 minutes at the same temperature
  3. extractionfollowed by extraction with ethyl acetate four times
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate, which
  5. concentrationwas then concentrated
  6. customThe concentrate was purified by means of a column chromatography (carrier: silica gel, 200 g, developing solvent: ethyl acetate-hexane, 4:1)

Sources & evidence

ORD record
ord-3d7c25213975492ab110cdaa96995548
Source dataset
uspto-grants-2001_01
Patent number
US06174877B1

Reaction notes

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