Category: 99662-34-7

Synthetic Route of 99662-34-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 99662-34-7 name is 4-Pyrazol-1-yl-benzaldehyde, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

[0419] A mixture of 4-(1H-pyrazol-1-yl)benzaldehyde (prepared as described in J. Med Chem. 1998, 41, 2390) (1.65 g, 9.58 mmol), (1,3-dioxolan-2-ylmethyl)triphenylphosphonium bromide (6.45 g, 15.02 mmol), and TDA-1 (3.20 mL, 10.00 mmol) in dichloromethane (50 mL) and sat. aq. K2CO3 (50 mL) was heated to reflux for 20 h. The layers were separated and the aqueous layer was extracted with dichloromethane (2×25 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried (MgSO4), and concentrated. THF (25 mL) and 10% HCl (25 mL) were added and the mixture was stirred for 1 h at rt. The reaction mixture was cooled to 0 C., made basic with 10% NaOH, and extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 3:1 hexane/ethyl acetate) provided 1.69 g (89%) of the title compound as a yellow solid. MS 199 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Pyrazol-1-yl-benzaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Henninger, Todd C.; Macielag, Mark J.; Marinelli, Brett A.; Zhu, Bin; US2004/18994; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 99662-34-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 99662-34-7 name is 4-Pyrazol-1-yl-benzaldehyde, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a cooled solution of 4-(pyrazol-l-yl)benzaldehyde (3.0 g, 0.017 mole) in methanol (20 mL) under N2, was added sodium borohydride (0.79 g, 0.02 mole) in portion wise. The reaction mixture was warmed to RT and stirred for 2 h. The reaction mixture was concentrated under vacuum, dissolved in ice cold water (75 mL) and extracted with ethyl acetate (100 mL x 2). Organic layer was washed with brine solution (50 mL), dried over Na2S04 and concentrated under vacuum to obtain the crude compound which was further purified by flash chromatography using ethyl acetate: n-hexane (40:60) to get l-(4- hydroxymethylphenyl) – 1 H-pyrazole . (0225) Yield: 2.4 g; 1H – NMR (DMSO- 6, 400 MHz) d ppm: 4.52 – 4.53 (d, J = 5.6 Hz, 2H), 5.23 – 5.26 (t, J = 5.7 Hz, 1H), 6.52 (s, 1H), 7.41 – 7.43 (d, J = 8.3 Hz, 2H), 7.72 (s, 1H), 7.77 – 7.79 (d, J = 8.3 Hz, 2H), 8.09 (d, J = 2.3 Hz, 1H); Mass (m/z): 175.1 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Pyrazol-1-yl-benzaldehyde, and friends who are interested can also refer to it.