Tetrahydro-2H-pyran-4-yl methanesulfonate Chemical Properties

Melting point:

47-49°C

Boiling point:

329.1±31.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Dichlromethane, DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Solid

color 

Off-White to Pale Beige

Stability:

Moisture Sensitive

InChI

InChI=1S/C6H12O4S/c1-11(7,8)10-6-2-4-9-5-3-6/h6H,2-5H2,1H3

InChIKey

GSEZHCLWHDZJAB-UHFFFAOYSA-N

SMILES

C1OCCC(OS(C)(=O)=O)C1

Safety Information

HS Code 

2932990090

Tetrahydro-2H-pyran-4-yl methanesulfonate Usage And Synthesis

Uses

Tetrahydro-2H-pyran-4-yl Methanesulfonate is an intermediate in the synthesis of 3,4,5-Trimethoxy-2-nitro Acetophenone (T795510). 3,4,5-Trimethoxy-2-nitro acetophenone is an intermediate used to prepare substituted 4-alkyl-2(1H)-quinazolinones as potential cardiotonics. It can be also used as an intermediate to synthesize 2-Amino-3,4,5-trimethoxybenzophenones as potent tubulin polymerization inhibitors.

Synthesis

In 200 mL of dichloromethane, tetrahydro-2H-pyran-4-ol (15.83 g, 0.155 mol) was mixed with triethylamine (21.6 mL, 0.155 mol) and dimethylaminopyridine (1.89 g, 0.015 mol) was added as a catalyst. Methanesulfonyl chloride (12 mL, 0.155 mol) was slowly added dropwise at 0 °C. After the dropwise addition, the reaction mixture was gradually warmed up to room temperature and stirred continuously for 16 hours. After completion of the reaction, the organic phase was washed sequentially with deionized water and brine, and then dried with anhydrous magnesium sulfate. After filtration to remove the drying agent, the solvent was removed by distillation under reduced pressure to afford tetrahydro-2H-pyran-4-yl methanesulfonate (Compound 1010, 22.6 g, 80.9% yield) as a yellow solid. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 4.90 (qn, J = 4.2 Hz, 1H), 3.95 (dt, J = 12.0, 4.2 Hz, 2H), 3.59-3.51 (m, 2H), 3.04 (s, 3H), 2.08-2.01 (m, 2H), 1.94-1.82 (m, 2H).

References

[1] Patent: US2009/156610, 2009, A1. Location in patent: Page/Page column 33
[2] Patent: US2010/210674, 2010, A1. Location in patent: Page/Page column 7-8
[3] Patent: US2014/45814, 2014, A1. Location in patent: Paragraph 0245; 0246
[4] Patent: WO2014/151106, 2014, A1. Location in patent: Paragraph 00187
[5] Patent: US2016/168156, 2016, A1. Location in patent: Paragraph 0503; 0504

Tetrahydro-2H-pyran-4-yl methanesulfonate(134419-59-3)Related Product Information

• TETRAHYDRO-PYRAN-3-YLAMINE HYDROCHLORIDE
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• METHYL TETRAHYDRO-4-OXO-2H-THIOPYRAN-3-CARBOXYLATE
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• Tetrahydropyran-4-SulfonylChloride
• 2-HYDROXYTETRAHYDROPYRAN
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• ethyl tetrahydro-2H-pyran-2-carboxylate
• METHYL TETRAHYDROPYRAN-3-CARBOXYLATE