3,6-Dichloropicolinaldehyde → HCID 86761704, compound

HRID 1880583Notes

Reaction equation

HRID 1880583 reaction equation
[CH3:1][Mg]Br.[Cl:4][C:5]1[C:6]([CH:12]=[O:13])=[N:7][C:8]([Cl:11])=[CH:9][CH:10]=1>C1COCC1>[Cl:4][C:5]1[C:6]([CH:12]([OH:13])[CH3:1])=[N:7][C:8]([Cl:11])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 108211483,6-DichloropicolinaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 86761704HCID 86761704, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl magnesium bromide (3.0M Et2O, 0.25 mL, 0.75 mmol) was added dropwise to a THF (2 mL) solution of 3,6-dichloropyridine-2-carbaldehyde (100 mg, 0.57 mmol) cooled to 0° C. After 1 hour the solution was partitioned between ethyl acetate and 1N aqueous HCl. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compound. 1H NMR (500 MHz, CDCl3): δ 7.67 (d, J=8.4 Hz, 1H); 7.30 (d, J=8.2 Hz, 1H); 5.22-5.14 (m, 1H); 3.83 (d, J=8.7 Hz, 1H) 1.50 (d, J=6.5 Hz, 3H). LCMS1 2.40 min. (M−H2O)=174

Workup

  1. customAfter 1 hour the solution was partitioned between ethyl acetate and 1N aqueous HCl
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-16a1e5653ba847e897c05104c1ec33c1
Source dataset
uspto-grants-2012_11
Patent number
US08318760B2

Reaction notes

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