5-(Hydroxymethyl)-1-methyl-1H-pyrazole synthesis
- Product Name:5-(Hydroxymethyl)-1-methyl-1H-pyrazole
- CAS Number:84547-61-5
- Molecular formula:C5H8N2O
- Molecular Weight:112.13
16034-46-1
84547-61-5
1-Methyl-1H-pyrazole-5-carboxylic acid (2 g, 15.86 mmol) was dissolved in tetrahydrofuran (50 mL) at 0 °C and in an inert atmosphere, followed by batchwise addition of lithium aluminum hydride (LiAlH4, 720 mg, 18.97 mmol). The reaction system was stirred under nitrogen protection at room temperature for 2 hours. Upon completion of the reaction, water (2 mL) was slowly added to quench the reaction. The mixture was dried over anhydrous sodium sulfate and filtered to remove the solid. The filtrate was concentrated under reduced pressure to afford the target product (1-methyl-1H-pyrazol-5-yl)methanol as a colorless oil (1.2 g, 67% yield). Mass spectrum (ESI, m/z): [M + H]+ 113.0. 1H NMR (300 MHz, CDCl3) δ 7.36 (d, J = 1.8 Hz, 1H), 6.18 (d, J = 1.8 Hz, 1H), 4.66 (s, 2H), 3.88 (s, 3H).
17827-60-0
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84547-61-5
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$14.00/100mg
Yield: 83.3%
Reaction Conditions:
with lithium aluminium tetrahydride in tetrahydrofuran at 0 - 20; for 12 h;
Steps:
1.2 Step 2: (l-methyl-lH-pyrazol-5-yl)methanol
To a stirred solution of methyl l-methyl-lH-pyrazole-5-carboxylate (3 g, 21.4 mmol) in tetrahydrofuran (50 mL) at 0 °C was added lithium aluminum hydride (977 mg, 25.7 mmol). The mixture was stirred at room temperature for 12 h. The reaction was quenched by adding water, extracted with ethyl acetate (100 mL), dried, concentrated and the residue was purified by column chromatography on silica gel (petroleum ether/ acetic ester =10: 1), to afford the title compound as an off-white oil (2 g, 83.3%).
References:
CONSTELLATION PHARMACEUTICALS, INC.;ALBRECHT, Brian, K.;AUDIA, James, Edmund;COOK, Andrew;COTE, Alexandre;DAKIN, Les, A.;GEHLING, Victor, S.;HARMANGE, Jean-Christophe;NASVESCHUK, Christopher, G.;VASWANI, Rishi, G. WO2014/151142, 2014, A1 Location in patent:Paragraph 0093
16034-46-1
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$6.00/1g
84547-61-5
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$14.00/100mg
27258-33-9
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84547-61-5
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$14.00/100mg
84547-59-1
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$90.00/50mg
84547-61-5
93 suppliers
$14.00/100mg