Water → 5-(1,3-Dioxolan-2-yl)picolinaldehyde

HRID 1881830Notes

Reaction equation

HRID 1881830 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][N:3]=1.CCCCCC.C([Li])CCC.CN(C)[CH:26]=[O:27].O>O1CCCC1>[O:9]1[CH2:10][CH2:11][O:12][CH:8]1[C:5]1[CH:6]=[CH:7][C:2]([CH:26]=[O:27])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 184696682-Bromo-5-(1,3-dioxolan-2-YL)pyridineHCID 178418244HCID 178418244, compound

Product 1

HCID 592551735-(1,3-Dioxolan-2-yl)picolinaldehydeYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-bromo-5-(1,3-dioxolan-2-yl)pyridine (9.60 g) in tetrahydrofuran (150 mL) was slowly added a 1.6M n-butyllithium hexane solution (28.7 mL) at −78° C. The reaction mixture was stirred for 30 min, N,N-dimethylformamide (3.9 mL) in tetrahydrofuran (50 mL) was added, and the mixture was warmed to room temperature and stirred for 30 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate solution. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (2.70 g, yield 36%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio). MS: 180 (MH+).

Workup

  1. stirringstirred for 30 min
  2. extractionthe mixture was extracted with ethyl acetate solution
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9da749f5ad86445cb7798c615e7ac3b1
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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