3-Hydroxybenzenethiol → 3-[(tetrahydro-2H-pyran-4-ylmethyl)sulfanyl]phenol

HRID 384460Notes

Reaction equation

HRID 384460 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C[O-].[Na+].CO.Br[CH2:15][CH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>CO>[O:19]1[CH2:20][CH2:21][CH:16]([CH2:15][S:1][C:2]2[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=2)[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 27366133-HydroxybenzenethiolHCID 27732864-(Bromomethyl)oxaneHCID 23694274Sodium methanolate methanol

Product 1

HCID 595272373-[(tetrahydro-2H-pyran-4-ylmethyl)sulfanyl]phenolYield 59.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Sulfanylphenol (250 mg) was dissolved in methanol (5 mL), and a 28% sodium methoxide-methanol solution (0.5 mL) was added thereto, followed by stirring at room temperature for 10 minutes. 4-(Bromomethyl)tetrahydro-2H-pyrane (410 mg) was added to the reaction mixture, followed by stirring at room temperature for 3 hours. The solvent was evaporated under reduced pressure, and then water was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried. The solvent was evaporated under reduced pressure, and the residue was washed with hexane to obtain 3-[(tetrahydro-2H-pyran-4-ylmethyl)sulfanyl]phenol (265 mg).

Workup

  1. stirringby stirring at room temperature for 3 hours
  2. customThe solvent was evaporated under reduced pressure
  3. additionwater was added to the residue
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. customdried
  7. customThe solvent was evaporated under reduced pressure
  8. washthe residue was washed with hexane

Sources & evidence

ORD record
ord-a50ed59e16d641e1a36b653522c88244
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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