2-Bromo-6-(1,3-dioxolan-2-yl)pyridine → HCID 89853573, compound

HRID 931087Notes

Reaction equation

HRID 931087 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[N:3]=1.C([Li])CCC.[O:18]1[CH2:21][C:20](=[O:22])[CH2:19]1>O1CCCC1>[O:9]1[CH2:10][CH2:11][O:12][CH:8]1[C:4]1[N:3]=[C:2]([C:20]2([OH:22])[CH2:21][O:18][CH2:19]2)[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 1186132-Bromo-6-(1,3-dioxolan-2-yl)pyridineHCID 150242543-OxetanoneHCID 178418339Butyllithium

Product 1

HCID 89853573HCID 89853573, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-bromo-6-(1,3-dioxolan-2-yl)pyridine (2.49 g, 10.8 mmol) in anhydrous tetrahydrofuran (40 mL) was added a solution of n-butyllithium (2.5 M, 4.3 mL, 10.8 mmol) at −78° C. After stirring for 30 min., a solution of oxetan-3-one (0.6 g, 8.32 mmol) in anhydrous tetrahydrofuran (12 mL) was added slowly and the mixture was stirred at that temperature for 1 h. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the crude compound. The crude material was purified via preparative TLC eluting with 35% ethyl acetate in petroleum ether to afford 3-(6-(1,3-dioxolan-2-yl)pyridin-2-yl)oxetan-3-ol (500 mg, 27%). MS (ES+) (M+H) 224.20; LCMS retention time: 2.76 minutes (Method S).

Workup

  1. stirringthe mixture was stirred at that temperature for 1 h
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto afford the crude compound
  9. customThe crude material was purified via preparative TLC
  10. washeluting with 35% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-8e1ba8432d604ab0a3ab620def49ed29
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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