Water → 5-(2,2-Dimethyl-1,3-dioxolan-4-yl)pyridine-2-carbaldehyde

HRID 1881840Notes

Reaction equation

HRID 1881840 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][O:11][C:10]([CH3:14])([CH3:13])[O:9]2)=[CH:4][N:3]=1.CCCCCC.C([Li])CCC.CN(C)[CH:28]=[O:29].O>C(OCC)C>[CH3:13][C:10]1([CH3:14])[O:9][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([CH:28]=[O:29])=[N:3][CH:4]=2)[CH2:12][O:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 469414392-Bromo-5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridineHCID 178418244HCID 178418244, compound

Product 1

HCID 469414405-(2,2-Dimethyl-1,3-dioxolan-4-yl)pyridine-2-carbaldehydeYield 27.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-bromo-5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridine (4.12 g) in diethyl ether (100 mL) was slowly added a 1.6M n-butyllithium hexane solution (10 mL) at −78° C. The reaction mixture was stirred for 30 min, and N,N-dimethylformamide (1.40 g) was added. The reaction mixture was warmed to room temperature over 1 hr, and stirred overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. 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 (900 mg, yield 27%) was obtained as a pale-yellow oil from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio). MS: 208 (MH+).

Workup

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

Sources & evidence

ORD record
ord-b70778ee1ed34c809b36895e96736f5f
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

Loading…