(TETRAHYDRO-2H-PYRAN-4-YL)METHANOL Chemical Properties

Boiling point:

105 °C

Density 

1.000±0.06 g/cm3(Predicted)

Flash point:

61°(142°F)

refractive index 

1.4600

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

pka

14.85±0.10(Predicted)

color 

Colorless to Light yellow to Light orange

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C6H12O2/c7-5-6-1-3-8-4-2-6/h6-7H,1-5H2

InChIKey

YSNVSVCWTBLLRW-UHFFFAOYSA-N

SMILES

C1OCCC(CO)C1

CAS DataBase Reference

14774-37-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22-41-37/38

Safety Statements 

26-36/37/39-23-39

HazardClass 

IRRITANT

HS Code 

29329990

(TETRAHYDRO-2H-PYRAN-4-YL)METHANOL Usage And Synthesis

Chemical Properties

Colorless liquid

Uses

Used as a reagent in the identification and optimization of pteridinone Toll-like receptor 7 agonists, which can be used for the oral treatment of viral hepatitis. 4-(Hydroxymethyl)tetrahydropyran is also a starting material for [1-[(Tetrahydro-2H-pyran-4-yl)methyl]-1H-indol-3-yl](2,2,3,3-tetramethylcyclopropyl)methanone which is a drug that acts as CB2 cannabinoid receptor agonist.

Synthesis

Ethyl tetrahydro-2H-pyran-4-carboxylate (5.0 g, 34.7 mmol) was slowly added to a stirred suspension of lithium aluminum hydride (LiAlH4, 4.0 g, 104 mmol) in tetrahydrofuran (THF, 100 mL) at 0 °C. The reaction mixture was kept stirred at 0 °C for 1 hour. Subsequently, ethyl acetate (20 mL) was added slowly and dropwise to the reaction mixture to quench the excess LiAlH4, followed by the addition of 10% aqueous sodium hydroxide (NaOH). The resulting mixture was continued to be stirred for 30 minutes. Upon completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad to remove insoluble impurities. The filtrate was concentrated under reduced pressure to give the target product (tetrahydro-2H-pyran-4-yl) methanol (9) as a colorless oil. The yield was 3.9 g in 96% yield. The product was characterized by 1H NMR (400 MHz, DMSO-d5): δ 4.46 (broad single peak, 1H), 3.82 (double peak, J=8.0 Hz, 2H), 3.25-3.22 (multiple peaks, 4H), 1.62-1.52 (multiple peaks, 3H), 1.18-1.04 (multiple peaks, 1H).

References

[1] Patent: US2014/275043, 2014, A1. Location in patent: Paragraph 0415; 0416
[2] Justus Liebigs Annalen der Chemie, 1936, vol. 525, p. 292,294
[3] Patent: WO2010/96371, 2010, A2. Location in patent: Page/Page column 156

(TETRAHYDRO-2H-PYRAN-4-YL)METHANOL(14774-37-9)Related Product Information

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