Methanol → Methyl 2-Methyltetrahydrofuran-2-carboxylate

HRID 386900Notes

Reaction equation

HRID 386900 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]1([C:11]([OH:13])=[O:12])[CH2:10][CH2:9][CH2:8][O:7]1.[CH3:14]O>>[CH3:5][C:6]1([C:11]([O:13][CH3:14])=[O:12])[CH2:10][CH2:9][CH2:8][O:7]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 31643262-Methyloxolane-2-carboxylic acid

Product 1

HCID 53486303Methyl 2-Methyltetrahydrofuran-2-carboxylateYield 93%

Procedure

Thionyl chloride (0.15 mL, 2.1 mmol) is added dropwise at 0° C. to a solution of 2-methyltetrahydro-2-furancarboxylic acid (250 mg, 1.9 mmol) in methanol (2.0 mL). After bringing the reaction mixture to room temperature, it is heated under reflux for 1 h. The solvent is removed under reduced pressure, the crude is dissolved in DCM and filtered through a pad of silica. Removal of the solvent under reduced pressure affords 276.0 mg of methyl 2-methyltetrahydro-2-furancarboxylate that is used in the next step without further purification. Yield: 93%. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.49 (3H, s), 1.78-1.85 (1H, m), 1.91-1.99 (2H, m), 2.30-2.37 (1H, m), 3.75 (3H, s), 3.92-4.02 (2H, m).

Workup

  1. customto room temperature
  2. temperatureit is heated
  3. temperatureunder reflux for 1 h
  4. customThe solvent is removed under reduced pressure
  5. dissolutionthe crude is dissolved in DCM
  6. filtrationfiltered through a pad of silica
  7. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-044d485137a6469c98344a3dad7c210a
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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