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CAS No. : | 10419-77-9 | MDL No. : | MFCD00041386 |
Formula : | C5H12IO3P | Boiling Point : | - |
Linear Structure Formula : | (CH3CH2O)2POCH2I | InChI Key : | PNFHTBDRPOJJTQ-UHFFFAOYSA-N |
M.W : | 278.03 | Pubchem ID : | 82616 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(5-Oxo-2, 2-bis-trifluoromethyl- [1, 3] oxathiolan-4-yl) -acetic acid (0.70 g, 2.3 mmol) was dissolved in anhydrous DMF (6 mL) and piperidine-2-carboxylic acid methyl ester hydrochloride (0.38 g, 2.1 mmol) was added to the stirred reaction mixture, followed by dropwise addition of DIEA (0.79 mL, 0.60 g, 4.7 mrnol). After 80 min at room temperature, the solvent was removed in vacuo and the residue was dissolved in ethyl acetate (60 mL). The solution was extracted with aqueous HCl (2 M, 2 x 4 mL), dried over Na2S04, filtered, and concentrated in vacuo. The residue was dissolved in a mixture of water (8 mL) and dioxane (3 mL). Iodomethyl-phosphonic acid diethyl ester (0.65 g, 2.3 mmol) and subsequently NaHCO3 (0.59 g, 7.0 mmol) were added to the stirred reaction mixture. After stirring for 14 h at 55 °C, the reaction mixture was concentrated in vacuo to a volume of approximately 10 mL. 1 M aqueous Na2CO3 (4 mL) was added and the aqueous solution was extracted with ethyl acetate (10 mL). The aqueous layer was then acidified with 6 M aqueous HC1 to pH 1 and extracted with ethyl acetate (3 x 30 mL). The combined organic layers were dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by flash chromatography over silica gel (elution with DCM/methanol/acetic acid 40: 10: 1) to give the title compound as a colorless oil. MS (m/z) : 426.5 [M+H]. |
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