Water → HCID 86731312, compound

HRID 2277239Notes

Reaction equation

HRID 2277239 reaction equation
[F:1][C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][N:5]=[C:4]([CH2:12][OH:13])[CH:3]=1.C(N(CC)CC)C.O>CS(C)=O>[F:1][C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][N:5]=[C:4]([CH:12]=[O:13])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 86731311HCID 86731311, compound

Product 1

HCID 86731312HCID 86731312, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (4-fluoro-5-(methoxymethoxy)pyridin-2-yl)methanol (3.59 g) and triethylamine (8.02 mL) in DMSO (30 mL) was added sulfur trioxide pyridine complex (9.16 g), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (2.43 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2fe56a91136240cdb6f56c018dd7146d
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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