3-Fluoro-5-[4-(methylsulfanyl)oxan-4-yl]phenol → HCID 18920179, compound

HRID 1291056Notes

Reaction equation

HRID 1291056 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:9]2([S:15][CH3:16])[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.C[OH:18].O>>[OH:1][C:2]1[CH:3]=[C:4]([C:9]2([S:15]([CH3:16])=[O:18])[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

3

Reactant 2

HCID 189202153-Fluoro-5-[4-(methylsulfanyl)oxan-4-yl]phenolHCID 22242641Methanol--water (1/1)

Product 1

HCID 18920179HCID 18920179, compoundYield 94%

Procedure

To a stirred solution of 4-(3-hydroxy-5-fluorophenyl)-4-methylthio-3,4,5,6-tetrahydro-2H-pyran (749 mg, 3.1 mmol)(EP 462830 A2 (1991)) in methanol-water (1:1.v/v; 20 ml) cooled to 0° C. was added NalO4 (710 mg, 3.3 mmol), the ice bath removed and the mixture stirred at room temperature for 2 hours. The reaction mixture was poured into water (50 ml) and extracted with ethyl acetate (50 ml). The organic extract was washed with water (50 ml), brine (50 ml), dried (MgSO4) and concentrated in vacuo. The residual solids were purified by column chromatography on silica gel (SiO2, 150 g; ethyl acetate) to afford 752 mg (94%) of the titled compound as white solids.

Workup

  1. additionwas added NalO4 (710 mg, 3.3 mmol)
  2. customthe ice bath removed
  3. additionThe reaction mixture was poured into water (50 ml)
  4. extractionextracted with ethyl acetate (50 ml)
  5. extractionThe organic extract
  6. washwas washed with water (50 ml), brine (50 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe residual solids were purified by column chromatography on silica gel (SiO2, 150 g; ethyl acetate)

Sources & evidence

ORD record
ord-d3ac465263f5420f9aef6b690d14c25f
Source dataset
uspto-grants-1998_05
Patent number
US05753682

Reaction notes

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