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CAS No. : | 100189-17-1 | MDL No. : | MFCD09926432 |
Formula : | C8H11NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CRZJKFRQNPDUIV-UHFFFAOYSA-N |
M.W : | 137.18 | Pubchem ID : | 13566816 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20℃; for 1.0h; | To a stirred solution of 2-(6-methylpyridin-3-yl) acetic acid (1 .5g, 9.9 mmol) in dry THF(20 mL) was added Borane-DMS (2 mL, 19.8 mmol) drop wise at 0 00. The reactionmixture was stirred at RT for lh. Reaction completion was monitored by TLC. Reactionmixture was quenched with methanol at 0 00 The reaction mixture was concentratedcompletely and extracted with ethyl acetate, washed with water (2 x 10 mL), sodium bicarbonate (2 x 10 mL) and brine solution (2 x 10 mL). Combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated and the crude mass obtained was purified by flash column chromatography to get the title product as pale yellow liquid. 1HNMR (400 MHz, DMSO-d6): 6 8.55 (s, 1H), 7.93 (dd, J = 8.0, 1.9 Hz, 1H), 7.56 (d, J =8.0 Hz, 1H), 4.74 (s, 1H), 3.65-3.60 (m, 2H), 2.77 (t, J = 6.2 Hz, 2H), 2.59 (s, 3H).LCMS: (Method B) 138.2 (M+H), Rt. 3.5 mm, 91.6% (Max). | |
With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20℃; for 1.0h; | Step 3: 2-(6-methylpyridin-3-yl) ethan-1-ol To a stirred solution of 2-(6-methylpyridin-3-yl) acetic acid (1.5g, 9.9 mmol) in dry THF (20 mL) was added Borane-DMS (2 mL, 19.8 mmol) drop wise at 0 C. The reaction mixture was stirred at RT for 1 h. Reaction completion was monitored by TLC. Reaction mixture was quenched with methanol at 0 C. The reaction mixture was concentrated completely and extracted with ethyl acetate, washed with water (2 * 10 mL), sodium bicarbonate (2 * 10 mL) and brine solution (2 * 10 mL). Combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated and the crude mass obtained was purified by flash column chromatography to get the title product as pale yellow liquid. 1H NMR (400 MHz, DMSO-d6): delta 8.55 (s, 1 H), 7.93 (dd, J = 8.0, 1.9 Hz, 1 H), 7.56 (d, J = 8.0 Hz, 1 H), 4.74 (s, 1 H), 3.65-3.60 (m, 2H), 2.77 (t, J = 6.2 Hz, 2H), 2.59 (s, 3H). LCMS: (Method B) 138.2 (M+H)+, Rt. 3.5 min, 91.6% (Max). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With triethylamine; In dichloromethane; at 0 - 20℃; for 1.0h; | To a stirred solution of <strong>[100189-17-1]2-(6-methylpyridin-3-yl)ethan-1-ol</strong> (0.5 g, 3.6 mmol) in dry DCM(10 mL) at 0 00 was added triethyl amine (1.5 mL, 10.8 mmol, Spectrochem) followed byaddition of methane sulfonyl chloride (0.4 mL, 5.4 mmol, Spectrochem). Reaction mass was brought to RT and stirred for 1 h. Reaction completion was monitored by TLC. Reaction mass was diluted with DCM, washed with water, dried over Na2SO4 and evaporated. The crude was isolated as pale brown liquid and was taken for next stepwithout any further purification (0.36 g, 46%). 1H NMR (400 MHz, DMSO-d6): 6 8.63 (s,1H), 8.00 (dd, J = 8.0, 1.8 Hz, 1H), 7.62-7.58 (m, 1H), 4.45 (t, J = 6.4 Hz, 2H), 3.14 (s,3H), 3.07 (d, J = 6.4 Hz, 2H), 2.59 (s, 3H). LCMS: (Method A) 216.0 (M+H), Rt. 3.3 mm,50.2% (Max). |
46% | With triethylamine; In dichloromethane; at 0 - 20℃; | Step 4: 2-(6-methylpyridin-3-yl) ethyl methanesulfonate To a stirred solution of <strong>[100189-17-1]2-(6-methylpyridin-3-yl)ethan-1-ol</strong> (0.5 g, 3.6 mmol) in dry DCM (10 mL) at 0 C was added triethyl amine (1.5 mL, 10.8 mmol, Spectrochem) followed by addition of methane sulfonyl chloride (0.4 mL, 5.4 mmol, Spectrochem). Reaction mass was brought to RT and stirred for 1 h. Reaction completion was monitored by TLC. Reaction mass was diluted with DCM, washed with water, dried over Na2SO4 and evaporated. The crude was isolated as pale brown liquid and was taken for next step without any further purification (0.36 g, 46%). 1H NMR (400 MHz, DMSO-d6): delta 8.63 (s, 1 H), 8.00 (dd, J = 8.0, 1.8 Hz, 1 H), 7.62-7.58 (m, 1 H), 4.45 (t, J = 6.4 Hz, 2H), 3.14 (s, 3H), 3.07 (d, J = 6.4 Hz, 2H), 2.59 (s, 3H). LCMS: (Method A) 216.0 (M+H)+, Rt. 3.3 min, 50.2% (Max). |
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