p-Toluenesulfonic acid → Methyl oxolane-3-carboxylate

HRID 541207

Reaction equation

HRID 541207 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([C:6]([OH:8])=[O:7])[CH2:2]1.[CH3:9]C1C=CC(S(O)(=O)=O)=CC=1>CO>[O:1]1[CH2:5][CH2:4][CH:3]([C:6]([O:8][CH3:9])=[O:7])[CH2:2]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 4661317(R)-Tetrahydro-3-furoic acid

Product 1

HCID 10678263Methyl oxolane-3-carboxylateYield 5,122.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of tetrahydrofuran-3-carboxylic acid (540 mg, 4.65 mmol, 1.00 equiv) and TsOH (10 mg, 0.06 mmol, 0.01 equiv) in methanol (40 mL) was stiffed at 66° C. in an oil bath. After 16 h, the resulting mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in 10 mL of ether, washed with 1×20 mL of NaHCO3 (aq., sat.) followed by 3×20 mL of brine, and concentrated under reduced pressure to yield 0.40 g (66%) of the title compound as a colorless oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 10 mL of ether
  3. washwashed with 1×20 mL of NaHCO3 (aq., sat.)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-01dd4c6476c5410eb28962ad379a19c2
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Linked notes

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