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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1499004Generated: November 1, 2026

(Prop-2-yn-1-yl)cyclohexane → 2-Ethoxy-4-p-tolyl-6-(cyclohexylmethyl)-1,2-oxaphosphorin 2-oxide

https://huagongshe.com/reaction/1499004

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(Prop-2-yn-1-yl)cyclohexaneHCID 87265—
Reactant2-(Di-tert-butylphosphino)biphenylHCID 2734215—
ReactantEthyl hydrogen p-tolylethynylphosphonateHCID 71546601—
CatalystGoldHCID 23985—
Solvent1,1-DichloroethaneHCID 6365—
Product2-Ethoxy-4-p-tolyl-6-(cyclohexylmethyl)-1,2-oxaphosphorin 2-oxideHCID 9001924964%

Reaction Steps

A gold (Ag(I)) catalyst {[Au(JohnPhos)NCCH3]|SbF6—} [JohnPhos:(2-biphenyl)di-tert-butylphosphine] (11.3 mg, 0.015 mmol) was put into a reaction container, and dichloroethane (0.4 mL) was put thereinto. After stirring at room temperature for 5 minutes, ethyl hydrogen p-tolylethynylphosphonate (67.3 mg, 0.3 mmol) diluted with 0.5 mL of dichloroethane was added thereto, and finally, prop-2-ynylcyclohexane (73.2 mg, 0.6 mmol) was put thereinto. Then, when all of the starting materials disappeared in the TLC, the reaction was allowed to be completed. After the solvent was removed under low atmospheric pressure, the product was separated by chromatography to obtain 2-ethoxy-4-p-tolyl-6-(cyclohexylmethyl)-1,2-oxaphosphorin 2-oxide (66.5 mg, 64%) which is a title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09200019B2
Source datasetuspto-grants-2015_12
ORD IDord-b19218f2dab046939aa8f396b1d66b9a
Source noteuspto-grants-2015_12