Boron trifluoride etherate → 2-tert-Butyl-4-(pyrid-3-yl)-5-(2-bromophenyl)-1,3-dioxolane

HRID 1613648Notes

Reaction equation

HRID 1613648 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([OH:17])(O)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Br:15])[CH:2]=1.[CH3:18][C:19]([CH:22]=[O:23])([CH3:21])[CH3:20].B(F)(F)F.CCOCC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:19]([CH:22]1[O:17][CH:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Br:15])[O:23]1)([CH3:21])([CH3:20])[CH3:18]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 12417PivalaldehydeHCID 516892Sodium BicarbonateHCID 197741971-(Pyrid-3-yl)-2-(2-bromophenyl)-ethanediol

Product 1

HCID 197741992-tert-Butyl-4-(pyrid-3-yl)-5-(2-bromophenyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8 g (0.027 mol) of 1-(pyrid-3-yl)-2-(2-bromophenyl)-ethanediol and 4.5 g (0.0525 mol) of pivaldehyde were dissolved in 100 ml of methylene chloride. This was achieved by adding 4.35 ml (0.0525 mol) of boron trifluoride etherate dropwise at room temperature and stirring overnight. Thereafter, the mixture was poured onto ice water and was neutralized with NaHCO3 solution. The organic phase was washed with water, dried over Na2SO4 and filtered, and the filtrate was evaporated down. The crude product was purified by chromatography.

Workup

  1. additionThereafter, the mixture was poured onto ice water
  2. washThe organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe filtrate was evaporated down
  6. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-fd7d379506b446dc8fd996a227ed1ff7
Source dataset
uspto-grants-1993_03
Patent number
US05194441

Reaction notes

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