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

HRID 9532

Reaction equation

HRID 9532 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.[C:10](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 219302Oxane-4-carboxylic acid

Product 1

HCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl esterYield 99.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Tetrahydro-2H-pyran-4-carboxylic acid (1.00 g, 7.68 mmol) was slowly added to a stirred suspension of anhydrous potassium carbonate (1.17 g, 8.45 mmol) in acetone (40 mL), followed by dimethyl sulfate (0.8 mL, 8.45 mmol). The mixture was stirred and heated for 3 h. The inorganic salts were then removed by filtration and washed with acetone, and the filtrate was dried and concentrated to give methyl tetrahydro-2H-pyran-4-carboxylate (1.1 g, 99%), which was used in the next step without further purification. GC-MS m/z 145 (MH+); 1H NMR (300 MHz, CDCl3) δ 11.70–1.80 (m, 4H), 2.47–2.52 (m, 1H), 3.34–3.43 (m, 2H), 3.65 (s, 3H), 3.88–3.95 (m, 2H).

Workup

  1. temperatureheated for 3 h
  2. customThe inorganic salts were then removed by filtration
  3. washwashed with acetone
  4. customthe filtrate was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e3ba7497cd344fb1b0003b2107debd6a
Source dataset
uspto-grants-2006_08
Patent number
US07091228B2

Linked notes

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