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

HRID 1507514Notes

Reaction equation

HRID 1507514 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.S(Cl)(Cl)=O.[CH3:14]O>>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:14])=[O:8])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 219302Oxane-4-carboxylic acid

Product 1

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

Procedure

Into a solution of oxane-4-carboxylic acid (50 mg, 0.38 mmol, 1.00 equiv) in methanol (10 mL) was added thionyl chloride (46 mg, 0.39 mmol, 1.01 equiv) dropwise with stirring at room temperature. The resulting solution was stirred for 3 h at room temperature. Concentration under reducing pressure gave the title compound, which was used directly for next step without further purification (brown oil).

Workup

  1. stirringThe resulting solution was stirred for 3 h at room temperature
  2. concentrationConcentration

Sources & evidence

ORD record
ord-dc656824b07c46a692e8d89b018b4a9e
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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