(1,4-dimethyl-1H-pyrazol-5-yl)methanol synthesis

Yield:-

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 20; for 2 h;

Steps:

85.2 (4-methyl-lH-pyrazol-3-yl)methanol
L1AIH₄ (910 mg, 23.98 mmol) was added portion wise to a solution of ethyl 1 ,4- dimethyl-lH-pyrazole-5-carboxylate (3.2 g, 19.03 mmol) in tetrahydrofuran (20 mL) and the reaction was stirred for 2 h at room temperature. The reaction was then quenched by the addition of water (1 ml). The resulting solution was diluted with sodium hydroxide (15%) (1.82mL).The mixture was dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum to afford (l,4-dimethyl-lH-pyrazol-5-yl)methanol as a light yellow solid (2.5 g, crude). LCMS: (ES, m/z): [M+H]⁺ 127.0 H NMR (300 MHz, DMSO-i/₆, ppm) δ 7.13 (s, 1H), 5.08 - 5.03 (m, 1H), 4.42 (d, / = 5.10Hz, 2H), 37.5 (s, 3H), 1.97 (s, 3H) 3H)

References:

BIOENERGENIX;MCCALL, John;KELLY, Robert, C.;ROMERO, Donna, L. WO2014/66795, 2014, A1 Location in patent:Paragraph 0175