ChemicalBook CAS DataBase List Methyl tetrahydropyran-4-carboxylate

Methyl tetrahydropyran-4-carboxylate synthesis

9synthesis methods

Product Name:Methyl tetrahydropyran-4-carboxylate
CAS Number:110238-91-0
Molecular formula:C7H12O3
Molecular Weight:144.17

5337-03-1

77-78-1

110238-91-0

Tetrahydropyran-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 the dropwise addition of dimethyl sulfate (0.8 mL, 8.45 mmol). The reaction mixture was stirred under heating conditions for 3 hours. After completion of the reaction, the inorganic salts were removed by filtration and the filter cake was washed with acetone. The filtrates were combined, dried and concentrated to afford methyl tetrahydropyran-4-carboxylate (1.1 g, 99% yield), which was used in the subsequent reaction without further purification. The product was analyzed by GC-MS showing m/z 145 (MH+); 1H NMR (300 MHz, CDCl3) δ 1.70-1.80 (m, 4H), 2.47-2.52 (m, 1H), 3.34-3.43 (m, 2H), 3.65 (s, 3H), 3.88-3.95 (m, 2H).

5337-03-1
311 suppliers
$10.00/1 g

77-78-1
325 suppliers
$19.69/1ml

110238-91-0
216 suppliers
$13.00/5g

Yield:110238-91-0 99%

Reaction Conditions:

with potassium carbonate in acetone for 3 h;Heating / reflux;

Steps:

1 Step 1.
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).

References:

Bayer Pharmaceuticals Corporation US2004/224997, 2004, A1 Location in patent:Page 18

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4295-99-2 Synthesis