ChemicalBook CAS DataBase List TETRAETHYLENEGLYCOL MONOMETHYL ETHER

TETRAETHYLENEGLYCOL MONOMETHYL ETHER synthesis

8synthesis methods

Product Name:TETRAETHYLENEGLYCOL MONOMETHYL ETHER
CAS Number:23783-42-8
Molecular formula:C9H20O5
Molecular Weight:208.25

2H-Pyran, tetrahydro-2-(3,6,9,12-tetraoxatridec-1-yloxy)-

727986-31-4

23783-42-8

General procedure: Tetraethylene glycol monomethyl ether was synthesized from the compound (CAS: 727986-31-4). This was done as follows: to a solution of 2-(2,5,8,11-tetraoxatridecan-13-yloxy)tetrahydro-2H-pyran (280 mg, 0.96 mmol) in methanol (5 mL) was added pyridinium salt of p-toluenesulfonate (PPTS, 24 mg, 0.096 mmol) at 0 °C. The reaction mixture was slowly warmed from 0 °C to room temperature and stirred for 16 hours. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure to give the crude product. Subsequently, the crude product was purified using silica gel column chromatography with an eluent of 5% methanol/dichloromethane (v/v), resulting in the target compound 5-2A (180 mg, 0.87 mmol, 90% yield) as a pale yellow liquid.

727986-31-4
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23783-42-8
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Yield:23783-42-8 90%

Reaction Conditions:

with pyridinium p-toluenesulfonate in methanol at 0 - 20; for 16 h;

Steps:

5.B 2,5,8,1 1-Tetraoxatridecan- 13-ol (5-2A)
To a solution of 2-(2,5,8,l l-tetraoxatridecan-13-yloxy)tetrahydro-2H-pyran 5-lA (280 mg, 0.96 mmol) in MeOH (5 mL) was added PPTS (24 mg, 0.096 mmol) and stirred at 0 °C to RT for 16 hr. The reaction mixture was concentrated under reduced pressure to get crude compound. Obtained crude was purified using silica gel column chromatography 5% MeOH in DCM to afford 5-2A (180 mg, 0.87 mmol, 90% yield) as a pale yellow liquid

References:

COCRYSTAL PHARMA, INC.;JACOBSON, Irina C.;FEESE, Michael D.;LEE, Sam S. WO2016/154241, 2016, A1 Location in patent:Paragraph 328; 331

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