1-(Tetrahydro-2H-pyran-4-yl)ethanone Chemical Properties

Boiling point:

90-94℃/15mm

Density 

1.024

refractive index 

1.4530

storage temp. 

-20°C

form 

Liquid

color 

Colorless to pale yellow

InChI

InChI=1S/C7H12O2/c1-6(8)7-2-4-9-5-3-7/h7H,2-5H2,1H3

InChIKey

VNMXIOWPBADSIC-UHFFFAOYSA-N

SMILES

C(=O)(C1CCOCC1)C

Safety Information

Hazard Codes 

Xn

Risk Statements 

42-36

Safety Statements 

22-45-26

HS Code 

2933998090

1-(Tetrahydro-2H-pyran-4-yl)ethanone Usage And Synthesis

Uses

1-(Tetrahydro-2H-pyran-4-yl)ethanone is mainly used as an intermediate in organic synthesis and medicinal chemistry, and can be used in the synthesis of cell biology detection reagents. In organic synthetic transformations, the keto carbonyl group in 1-(Tetrahydro-2H-pyran-4-yl)ethanone can be reacted with Wittig's reagent to prepare a variety of polysubstituted olefinic compounds, and in addition, the keto carbonyl group can be reduced to a hydroxyl group by the corresponding reducing agent.

Synthesis

Example 1 (Synthesis of 4-acetyltetrahydropyran) In a 10 mL glass flask equipped with a stirring device, a thermometer and a reflux condenser, 0.38 g (2.0 mmol) of methyl 4-acetyltetrahydro-2H-pyran-4-carboxylate (synthesized according to the method of Reference Example 1) of 99% purity and 1.08 mL (10 mmol) of 9 mol/L sulfuric acid were added. The reaction mixture was heated to 120°C under stirring and the reaction lasted for 1.5 hours. Upon completion of the reaction, the reaction mixture was analyzed by gas chromatography (internal standard method) and the formation of 0.25 g (yield: 96%) of 4-acetyltetrahydropyran was confirmed.

References

[1] Patent: EP1700852, 2006, A1. Location in patent: Page/Page column 7-8
[2] Patent: EP1700852, 2006, A1. Location in patent: Page/Page column 8
[3] Patent: EP1700852, 2006, A1. Location in patent: Page/Page column 8
[4] Patent: EP1700852, 2006, A1. Location in patent: Page/Page column 8
[5] Patent: WO2011/50016, 2011, A1. Location in patent: Page/Page column 35-36

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