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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 465880Generated: October 29, 2026

Triphenylphosphine → HCID 131717570, compound

https://huagongshe.com/reaction/465880

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriphenylphosphineHCID 11776—
ReactantHCID 20571334HCID 20571334—
ReactantHCID 131717571HCID 131717571—
ReactantHCID 131717572HCID 131717572—
ReactantButyllithiumHCID 178418339—
CatalystHCID 178418390HCID 178418390—
SolventTolueneHCID 1140—
SolventDiethyl EtherHCID 3283—
ProductHCID 131717570HCID 131717570—

Reaction Steps

The intermediate product obtained in Example 24, i.e., 5β-cholane alcohol, 10 m mol, was subjected to tosylation and treated with lithium bromide, thus forming 8 m mol of 5β-cholane bromide. 5β-cholane bromide was made to react with 12 m mol of triphenylphosphine in toluene, thereby preparing 7.8 m mol of 5β-cholane-triphenylphosphonium bromide. This product, 7.5 m mol, was reacted with 7.5 m mol of p-dimethoxybenzaldehyde in ether in the presence of butyl lithium. The product resulting from this reaction was hydrogenated, by using palladium carbon as catalyst, whereby 7.0 m mol of 5β-cholane-p-dimethoxybenzene was obtained. This compound, 6.8 m mol, was treated with sodium in liquid ammonia, thus forming 5.1 m mol of 5β-cholane-cyclohexyl-1,4-dione. This product, 4.5 m mol, was made to react with 10 m mol of malononitrile. The reaction product was treated with bromine, thereby preparing 1.2 m mol of 5β-cholanetetracyanoquinodimethane, which is identified with the following formula: ##STR54##

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05153680
Source datasetuspto-grants-1992_10
ORD IDord-cfdd42175544483b8a5775c6f03652dc
Source noteuspto-grants-1992_10