p-Toluenesulfonic acid → 2H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester

HRID 541257Notes

Reaction equation

HRID 541257 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.[CH3:10]C1C=CC(S(O)(=O)=O)=CC=1>CO>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 219302Oxane-4-carboxylic acid

Product 1

HCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tetrahydro-2H-pyran-4-carboxylic acid (520 mg, 4.00 mmol, 1.00 equiv) in methanol (50 mL) was added PTSA (35.0 mg, 0.200 mmol). The resulting mixture was stirred overnight at 80° C. in an oil bath, then cooled to ambient temperature and concentrated in vacuo. The residue was diluted with 30 mL of water and extracted with 3×30 mL of DCM. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated in vacuo. This resulted in 500 mg (87%) of methyl tetrahydro-2H-pyran-4-carboxylate as a colorless oil.

Workup

  1. temperaturecooled to ambient temperature
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with 30 mL of water
  4. extractionextracted with 3×30 mL of DCM
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThis resulted in 500 mg (87%) of methyl tetrahydro-2H-pyran-4-carboxylate as a colorless oil

Sources & evidence

ORD record
ord-b9b34bcade8c4e658d5b55bfe2659c2c
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

Loading…