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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 926997Generated: October 31, 2026

Water → HCID 178501080, compound

https://huagongshe.com/reaction/926997

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantBenzyltriphenylphosphonium bromideHCID 2734970—
ReactantPotassium tert-butoxideHCID 23665647—
ReactantHCID 178501145HCID 178501145—
SolventTetrahydrofuranHCID 8028—
ProductHCID 178501080HCID 17850108018.7%

Reaction Steps

Benzyltriphenylphosphonium bromide (2.94 g) was dissolved in THF (23.0 mL), added at −20° C. with potassium tert-butoxide (1.07 g) in small portions, and stirred for 1 hour at the same temperature. Subsequently, a THF (6.0 mL) solution of methyl cis-4-formylcyclohexane carboxylate (1.00 g) was added dropwise over 35 minutes, and stirred for 1.6 hours at the same temperature. After raising the temperature to room temperature, it was stirred after adding water and extracted with toluene. The organic layer was washed with water and saturated brine in order. After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The residues were purified by silica gel column chromatography (9% ethyl acetate/hexane) to obtain the title compound (268 mg) as a colorless oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09290440B2
Source datasetuspto-grants-2016_03
ORD IDord-bd73194540a4416eb9c7c787dc6bd12f
Source noteuspto-grants-2016_03