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With manganese(IV) oxide; In acetone; at 60℃; for 4h;
To a stirred solution of lH-pyrazol-4- ylmethanol 19-3 (4000 mg, 40.77 mmol) in acetone (10 rnL) was added manganese dioxide (35.45 g, 407.73 mmol). The reaction mixture was heated at 60C for 4 hours and then filtered through celite and concentrated under reduced pressure. The crude material was purified by column chromatography at 2% methanol in dichloromethane to afford l H-pyrazole-4-carbaldehyde 19-4 (2.05 g, 21.33 mmol, 52.33% yield) as light yellow solid. 'H NMR (400 MHz, DMSO-d6) d 13.55 (hr s, 1 1 1 ), 9.84 (s, 1 1 1 ), 8.49 (br s, 1 1 1 ), 8.00 (br s, 1 1 1 ):
With manganese(IV) oxide; In acetone; at 20 - 60℃;
(1H-Pyrazol-4-yl)methanol (0.350 g, 3.57 mmol) was dissolved in acetone (20mL) and treated with Mn02 (1.55 g, 17.9 mmol). The mixture was heated at 60C underreflux for 5 h then left standing at rt overnight. The reaction mixture was diluted withadditional acetone and filtered through a pad of CELITE. Solids were washed withacetone, and the filtrate was evaporated. The residue was chromatographed on silica gel to furnish Intermediate 7 as a white crystalline solid (0.17 g, 50% over two steps). ?HNMR (500MHz, CDC13) oe 9.97 (s, 1H), 8.14 (s, 2H).
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