3-methoxy-tetrahydropyran-4-one Chemical Properties

Boiling point:

201.3±30.0 °C(Predicted)

Density 

1.08±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C6H10O3/c1-8-6-4-9-3-2-5(6)7/h6H,2-4H2,1H3

InChIKey

YMJJPBWCARDMCG-UHFFFAOYSA-N

SMILES

C1OCCC(=O)C1OC

Safety Information

HS Code 

2932990090

3-methoxy-tetrahydropyran-4-one Usage And Synthesis

Synthesis

The general procedure for the synthesis of 3-methoxy-tetrahydro-2H-pyran-4-one from the compound (CAS: 624734-16-3) was as follows: intermediate 3 (3.0 g, 17.04 mmol) was dissolved in a mixed solvent of tetrahydrofuran/water (60 mL/10 mL) and concentrated hydrochloric acid (6 mL) was added. The reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, the mixture was concentrated under reduced pressure to remove the tetrahydrofuran. Subsequently, the aqueous layer was extracted with ether (6 x 50 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and the solvent evaporated under reduced pressure to give Intermediate 24 (1.75 g, 79% yield) as a clear oil. The product was characterized by 1H NMR (500 MHz, CDCl3) with chemical shifts δ of 4.23 (ddd, J = 1.2, 11.4, 12.4 Hz, 1H), 4.15-4.09 (m, 1H), 3.82 (dd, J = 5.95, 8.7 Hz, 1H), 3.74 (ddd, J = 5.5, 8.5, 13.6 Hz. 1H), 3.56 (dd, J = 8.8, 11.3 Hz, 1H), 3.50 (s, 3H), 2.61 (app dd, J = 5.0, 8.9 Hz, 2H).

References

[1] Patent: WO2005/14537, 2005, A2. Location in patent: Page 49
[2] Patent: WO2003/93231, 2003, A2. Location in patent: Page/Page column 72
[3] Patent: WO2003/93266, 2003, A1. Location in patent: Page/Page column 20

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