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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1639815Generated: November 2, 2026

Sodium hydride → HCID 59334588, compound

https://huagongshe.com/reaction/1639815

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
ReactantDiethyl (cyanomethyl)phosphonateHCID 75676—
ReactantHCID 59334563HCID 59334563—
SolventTetrahydrofuranHCID 8028—
SolventAmmonium ChlorideHCID 25517—
ProductHCID 59334588HCID 5933458886.4%

Reaction Conditions

Temperature0 °C

Reaction Steps

To a solution of diethyl cyanomethylphosphonate (1.62 mL, 10.02 mmol) in tetrahydrofuran (70 mL) was added 60% sodium hydride (370 mg, 9.25 mmol) under ice-cooling, and the mixture was stirred at 0° C. for 30 min. To the mixture was added a solution of 7-chloro-2-methyl-2H-indazole-4-carbaldehyde (1.50 g, 7.71 mmol) in tetrahydrofuran (30 mL) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. The reaction solution was diluted with saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=15/85→40/60) to give the title compound (1.45 g, yield 86%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08110585B2
Source datasetuspto-grants-2012_02
ORD IDord-f8eec64496ef4aa78d322f36d908b7f9
Source noteuspto-grants-2012_02