Acetone → HCID 90386464, compound

HRID 2170160Notes

Reaction equation

HRID 2170160 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 and the reaction mixture was stirred at ambient temperature for 14 h. The reaction mixture was diluted with water (15 mL) and the resulting mixture extracted with ethyl acetate (2×50 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give a residue which was purified by column chromatography using 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%). LCMS Condition B-26: retention time 2.17, [M+2]=260.0. 1H NMR (400 MHz, CDCl3) δ 1.48 (s, 3H), 1.55 (s, 3H), 3.72 (dd, J=7.6 Hz, J=8.4 Hz, 1H), 4.36 (dd, J=6.4 Hz, J=8.4 Hz, 1H), 5.08 (dd, J=6.4 Hz, J=7.6 Hz, 1H), 7.85-7.86 (m, 1H), 8.49 (d, J=1.6 Hz, 1H), 8.62 (d, J=2.0 Hz, 1H).

Workup

  1. extractionthe resulting mixture extracted with ethyl acetate (2×50 mL)
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customto give a residue which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-01c4dfcecff14dd6a980a5901aab03fd
Source dataset
uspto-grants-2015_06
Patent number
US09050345B2

Reaction notes

Loading…