Methyl tetrahydropyran-4-carboxylate Chemical Properties

Melting point:

-33°C

Boiling point:

197°C

Density 

1.080 g/mL at 20 °C(lit.)

Flash point:

86°C

storage temp. 

Sealed in dry,Room Temperature

form 

liquid

color 

Clear

BRN 

114974

InChIKey

CNCMVGXVKBJYNU-UHFFFAOYSA-N

CAS DataBase Reference

110238-91-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36-36/37/38

Safety Statements 

26-37/39

RIDADR 

1993

WGK Germany 

2

Hazard Note 

Harmful

HS Code 

29329990

MSDS

• Language:English Provider:SigmaAldrich

Methyl tetrahydropyran-4-carboxylate Usage And Synthesis

Chemical Properties

colorless liquid

Uses

Methyl tetrahydro-2H-pyran-4-carboxylate may be used in the following syntheses:

• cycloalkylamide derivatives
• tetrahydro-2-furoic chloride
• tetrahydro-2H-pyran-4-carboxylic chloride

Synthesis

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).

References

[1] Patent: US2004/224997, 2004, A1. Location in patent: Page 18
[2] Journal of the American Chemical Society, 1993, vol. 115, # 18, p. 8401 - 8408

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