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CAS No. : | 443-73-2 | MDL No. : | MFCD00056921 |
Formula : | C10H8FNO2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | GWLLOJBOPVNWNF-UHFFFAOYSA-N |
M.W : | 193.17 | Pubchem ID : | 96750 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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 |
---|---|---|
100% | To a solution of 5-fluoroindole -3-acetic acid (ig, 5.2mmol) in THE (2Oml) was added a1M solution of lithium aluminium hydride in THE (10.4m1, 10.4mmol) and the mixturerefluxed for 1.5 hours. The mixture was cooled, 0.39m1 of water and then 0.39m1 of15% NaOH(aq) added, followed by I .2m1 of water. The precipitate was collected viavacuum filtration and the filtrate concentrated to give 2-(5-fluoro-1 H-indol-3-yl)ethanol,an orange oil (0.927g, 100%); ?H NMR (400 MHz, CHLOROEORM-d) 6 ppm 2.98 (t,J=6.41 Hz, 2 H)1 3.89 (t, J=6.18 Hz, 2 H), 6.95 (td, J9.04, 2.52 Hz, I H), 7.12 (s, 1 H), 7.22 - 7.30 (m, 2 H), 8.06 (br. S., 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
This example demonstrates a general procedure for the synthesis of 3- hydroxyethylindole derivatives 53-55 used in the preparation of compounds in accordance with an embodiment of the invention. See Figure 2.[0083] To a solution of a 2- and/or 5-substituted-indole-3-acetic acid in methanol is added />-toluenesulfonic acid monohydrate (3 eq), and the reaction mixture is stirred at 600C overnight. After neutralization with IN aqueous NaOH, the solvent is evaporated leaving an oily residue, which is dissolved in ethyl acetate. The solution is washed with water, dried over MgSO4, and filtered. The filtrate is evaporated leaving an oily residue, which is subjected to column flush chromatography on silica gel. Elution with a mixture of toluene and acetone (5:1) gives the corresponding ester.[0084] To a solution of the ester in THF is added lithium aluminum hydride (2.8 eq) at 0 0C, and the reaction mixture is stirred at 0 0C for 1 h and at room temperature for 1 h. After addition of ethyl acetate, the reaction mixture is stirred at room temperature for 30 min. The reaction mixture is diluted with ethyl acetate and washed with water, dried over MgSO4, and filtered. The filtrate is evaporated leaving an oily residue, which is subjected to column chromatography on silica gel. Elution with a mixture of toluene and acetone (3:1) gives the pure alcohol. |
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