p-Toluenesulfonic acid → 2-Fluoro-3-(2-hydroxyethoxymethyl)-5-methoxybenzaldehyde

HRID 1161580Notes

Reaction equation

HRID 1161580 reaction equation
C[O:2][CH:3](OC)[C:4]1[C:5]([F:23])=[C:6]([CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1)[CH2:7][O:8][CH2:9][CH2:10][O:11]C1CCCCO1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1.O>[F:23][C:5]1[C:6]([CH2:7][O:8][CH2:9][CH2:10][OH:11])=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:4]=1[CH:3]=[O:2]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 595174642-[2-(3-Dimethoxymethyl-2-fluoro-5-methoxybenzyloxy]ethoxy]tetrahydropyran

Product 1

HCID 595168732-Fluoro-3-(2-hydroxyethoxymethyl)-5-methoxybenzaldehydeYield 46.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2-[2-(3-Dimethoxymethyl-2-fluoro-5-methoxybenzyloxy]ethoxy]tetrahydropyran (1.035 g) was dissolved in 10 ml of THF and 3 ml of water, and 1 g of p-toluenesulfonic acid was added thereto. The resulting mixture was stirred at room temperature overnight, and then water was added thereto. The mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate) to give the title compound (305 mg).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe desiccating agent was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate)

Sources & evidence

ORD record
ord-44c6ed68584a4ab982010c1ac8f88781
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

Loading…