4-Cyanotetrahydro-4H-pyran Chemical Properties

Boiling point:

82-83 °C(Press: 10 Torr)

Density 

1.0343 g/cm3

refractive index 

1.4521

storage temp. 

2-8°C

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C6H9NO/c7-5-6-1-3-8-4-2-6/h6H,1-4H2

InChIKey

RLZJFTOYCVIYLE-UHFFFAOYSA-N

SMILES

C1OCCC(C#N)C1

Safety Information

RIDADR 

UN2811

HazardClass 

IRRITANT

HS Code 

2932990090

4-Cyanotetrahydro-4H-pyran Usage And Synthesis

Uses

Tetrahydro-2H-Pyran-4-Carbonitrile is used in preparation of substituted Amide compounds as farnesoid X receptor modulators.

Synthesis

The general procedure for the synthesis of 4-cyanotetrahydropyran from tetrahydropyran-4-carboxamide was as follows: thionyl chloride (10.0 mL, 137 mmol) was slowly added to tetrahydropyran-4-carboxamide (3.0 g, 23 mmol), and the reaction mixture was stirred under reflux for 4 hr. Upon completion of the reaction, the mixture was carefully decanted onto ice and the pH was adjusted with 50% sodium hydroxide solution to 14. Subsequently, the aqueous phase was extracted with ethyl acetate (3 x 50 mL), the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure to give a light yellow oily product (2.4 g, 94% yield) which did not require further purification. The structure of the product was confirmed by the following characterization data: IR (νmax, cm-1 ): 2961, 2932, 2851, 2240, 1468, 1446, 1390, 1242, 1125, 1066, 1011; 1H NMR (500 MHz, CDCl3): δ 3.91 (2H, ddd, J = 11.9, 6.3, 3.6 Hz, 2 × 3.6 Hz, 2 × 3.6 Hz, 2 × 3.9, 6.3, 3.6 Hz, 2 × 3.6 Hz). 3.6 Hz, 2×2-HA), 3.61 (2H, ddd, J = 11.9, 7.8, 3.3 Hz, 2×2-HB), 2.91-2.85 (1H, m, 4-H), 1.99-1.92 (2H, m, 2×3-HA), 1.91-1.84 (2H, m, 2×3-HB); 13C NMR (75 MHz, CDCl3): δ 121.2, 65.6, 28.9, 25.3; HRMS (ESI+): calculated value C6H10NO ([M+H]+): 112.0756, measured value: 112.0754, Δ -1.8 ppm.

References

[1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 11, p. 2629 - 2635
[2] Patent: US2007/111984, 2007, A1. Location in patent: Page/Page column 45
[3] Journal of the American Chemical Society, 1943, vol. 65, p. 370
[4] Patent: US2009/253679, 2009, A1. Location in patent: Page/Page column 54-55

4-Cyanotetrahydro-4H-pyran(4295-99-2)Related Product Information

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• 4-(3-BROMOPHENYL)TETRAHYDROPYRAN-4-CARBONITRILE
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• 4-CYANO-TETRAHYDROPYRAN-4-CARBOXYLIC ACID
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• 4-(Dimethylamino)tetrahydro-2H-pyran-4-carbonitrile
• 4-AMINOTETRAHYDRO-2H-PYRAN-4-CARBONITRILE
• 4-Cyanotetrahydro-4H-pyran