Acetone → HCID 90386464, compound

HRID 593710Notes

Reaction equation

HRID 593710 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:8]2[CH2:10][O:9]2)[CH:7]=1.B(F)(F)F.CCOCC.[CH3:20][C:21]([CH3:23])=[O:22]>O>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:8]2[CH2:10][O:9][C:21]([CH3:23])([CH3:20])[O:22]2)[CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 8000Boron trifluoride etherateHCID 86663364HCID 86663364, compound

Product 1

HCID 90386464HCID 90386464, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-bromo-5-(oxiran-2-yl)pyridine (1.00 g, 5.00 mmol) in acetone (25 mL) was added BF3.OEt2 (0.950 mL, 7.50 mmol) dropwise at ambient temperature and the reaction mixture was stirred for 14 h. The reaction mixture was diluted with water (15 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The resulting residue was purified by combiflash (REDISEP®, silica gel, 40 g, 25% EtOAc/hexanes) to obtain 3-bromo-5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridine (0.700 g, 54.2%) as a pale yellow liquid. LCMS (Condition 8): retention time 2.17 min, [M+2]=260.0. 1H NMR (400 MHz, CDCl3) δ 1.48 (s, 3 H), 1.55 (s, 3 H), 3.72 (dd, J=7.6 Hz, J=8.4 Hz, 1 H), 4.36 (dd, J=6.4 Hz, J=8.4 Hz, 1 H), 5.08 (dd, J=6.4 Hz, J=7.6 Hz, 1 H), 7.85-7.86 (m, 1 H), 8.49 (d, J=1.6 Hz, 1 H), 8.62 (d, J=2.0 Hz, 1 H).

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by combiflash (REDISEP®, silica gel, 40 g, 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c969d99068a741229f06c0397c15a8dc
Source dataset
uspto-grants-2016_01
Patent number
US09242966B2

Reaction notes

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