Sodium Hydroxide → (1-Methyl-5-phenyl-1H-pyrazol-3-yl)methanol

A stirred suspension of sodium borohydride (1.28 g) in dry tetrahydrofuran (80 mL) was treated with calcium chloride (1.88 g). The mixture was stirred for 1 hour then treated with a solution of ethyl 1-methyl-5-phenylpyrazol-3-ylcarboxylate (5.2 g, prepared according to the procedure described by Martins et al., J. Heterocycl. Chem. (1999), 36(1), 217–220) in dry tetrahydrofuran (40 mL). After stirring at room temperature for 3 days and at reflux temperature for 8 hours the mixture was treated with sodium hydroxide solution (50 mL, 1N). This mixture was stirred at room temperature for 1 hour, then evaporated to remove the organic solvents and then extracted three times with dichloromethane (140 mL). The combined extracts were washed with water, then dried over magnesium sulfate and then evaporated to give the title compound as a white solid, m.p. 95–99° C.

1. customprepared
2. stirringAfter stirring at room temperature for 3 days
3. temperatureat reflux temperature for 8 hours the mixture
4. stirringThis mixture was stirred at room temperature for 1 hour
5. customevaporated
6. customto remove the organic solvents
7. extractionextracted three times with dichloromethane (140 mL)
8. washThe combined extracts were washed with water
9. dry with materialdried over magnesium sulfate
10. customevaporated

ORD record

ord-2055f7cdd04f46baa4d7ec1d05778119

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07227020B2