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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1257394Generated: November 2, 2026

Water → HCID 86650592, compound

https://huagongshe.com/reaction/1257394

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantDimethylformamideHCID 6228—
ReactantHCID 66939482HCID 66939482—
ReactantButyllithiumHCID 178418339—
SolventTetrahydrofuranHCID 8028—
ProductHCID 86650592HCID 8665059264.4%

Reaction Steps

Under a nitrogen atmosphere at −78° C., to a solution (100 mL) of the compound (8.0 g, 23 mmol) obtained in Example 89a in tetrahydrofuran was added n-butyllithium (1.6M hexane solution, 18 mL, 28 mmol), and the mixture was stirred at the same temperature for 1 hr. Anhydrous N,N-dimethylformamide (2.3 mL, 30 mmol) was added to the reaction mixture, and the mixture was stirred at −78° C. for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=80/20) to give the title compound (5.5 g, 64%) as a pale-yellow solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08461348B2
Source datasetuspto-grants-2013_06
ORD IDord-4f2d25e12daa4ca8a78b6153ee3adaba
Source noteuspto-grants-2013_06