Water → 5-(2-Fluoro-5-methoxyphenyl)-6-neopentylpicolinealdehyde

HRID 1049527Notes

Reaction equation

HRID 1049527 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:11]=[CH:12][C:13]([CH2:21][OH:22])=[N:14][C:15]=1[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C.O>CS(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:11]=[CH:12][C:13]([CH:21]=[O:22])=[N:14][C:15]=1[CH2:16][C:17]([CH3:18])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 117759814(5-(2-Fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methanol

Product 1

HCID 1177598875-(2-Fluoro-5-methoxyphenyl)-6-neopentylpicolinealdehydeYield 93.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methanol (2.90 g) and triethylamine (13.3 mL) in DMSO (45 mL) was added sulfur trioxide pyridine complex (6.08 g), and the mixture was stirred at room temperature for 10 min. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. After silica gel filtration, the solvent was evaporated under reduced pressure to give the title compound (2.69 g) as a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter silica gel filtration
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5707f02458354ce6920691413dfa8228
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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