Dimethyl Sulfoxide → 2,4-Dichloro-6-methylnicotinaldehyde

HRID 1860428Notes

Reaction equation

HRID 1860428 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Cl:11][C:12]1[C:17]([CH2:18][OH:19])=[C:16]([Cl:20])[CH:15]=[C:14]([CH3:21])[N:13]=1.C(N(CC)CC)C>ClCCl>[Cl:11][C:12]1[C:17]([CH:18]=[O:19])=[C:16]([Cl:20])[CH:15]=[C:14]([CH3:21])[N:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 9267100(2,4-dichloro-6-methylpyridin-3-yl)methanol

Product 1

HCID 112524812,4-Dichloro-6-methylnicotinaldehydeYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

DMSO (14.2 mL, 200 mmol) was added to a stirred solution of oxalyl chloride (8.7 mmol, 99 mmol) in dichloromethane (100 mL) at −70° C. After 15 min, alcohol (10) (6.40 g, 33.3 mmol) in dichloromethane (25 mL) was added, followed by triethylamine (56 mL). The mixture was allowed to warm to room temperature and was stirred for 1 hour. The mixture was washed with aqueous sodium bicarbonate (75 mL), dried (MgSO4), and concentrated under vacuum. The residue was purified by column chromatography (elution with 10% ethyl acetate in hexanes) to afford 5.00 g (78%) of (11) as a pale yellow oil which solidified on standing: LCMS (MH+, 190), Rf 0.48 (20% ethyl acetate in hexanes).

Workup

  1. washThe mixture was washed with aqueous sodium bicarbonate (75 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by column chromatography (elution with 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b6b8a6b02a284077a3b4bb3a7630e802
Source dataset
uspto-grants-2003_03
Patent number
US06531475B1

Reaction notes

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