| Identification | Back Directory | [Name]
Tetrahydro-2H-pyran-4-yl methanesulfonate | [CAS]
134419-59-3 | [Synonyms]
oxan-4-yl methanesulfonate
Tetrahydropyran-4-yl methanesulfonate
4-Tetrahydropyranylmethanesulfonate,95%
Tetrahydro-1H-pyran-4-yl methanesulfonate
4-Tetrahydropyranyl Methanesulfonate, 95%
Tetrahydro-2H-pyran-4-ylmethanesulphonate
Tetrahydro-2H-pyran-4-yl methanesulfonate
2H-Pyran-4-ol, tetrahydro-, methanesulfonate | [Molecular Formula]
C6H12O4S | [MDL Number]
MFCD11505063 | [MOL File]
134419-59-3.mol | [Molecular Weight]
180.22 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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