Triphenylphosphine → HCID 131717570, compound

HRID 465880Notes

Reaction equation

HRID 465880 reaction equation
[Br-].[CH3:2][CH2:3][CH2:4][C@H:5]([C@@H:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([CH2:22][CH2:23]2)[C@:19]2([CH3:20])[C@@H:14]([CH2:15][CH2:16][CH2:17][CH2:18]2)[CH2:13][CH2:12]3)[CH2:9][CH2:8]1)[CH3:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCC[C@H]([C@@H]1[C@]2(C)[C@H]([C@H]3[C@H](CC2)[C@]2(C)[C@@H](CCCC2)CC3)CC1)C.[Br-].C1([PH+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:89][O:90][C:91]1([CH:98]=[CH:97][C:96]([O:99][CH3:100])=[CH:95][CH2:94]1)C=O.C([Li])CCC>C1(C)C=CC=CC=1.CCOCC.[C].[Pd]>[CH3:2][CH2:3][CH2:4][C@H:5]([C@@H:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([CH2:22][CH2:23]2)[C@:19]2([CH3:20])[C@@H:14]([CH2:15][CH2:16][CH2:17][CH2:18]2)[CH2:13][CH2:12]3)[CH2:9][CH2:8]1)[CH3:6].[CH3:89][O:90][C:91]1[CH:98]=[CH:97][C:96]([O:99][CH3:100])=[CH:95][CH:94]=1

Participants

9

Reactant 5

HCID 11776TriphenylphosphineHCID 20571334HCID 20571334, compoundHCID 131717571HCID 131717571, compoundHCID 131717572HCID 131717572, compoundHCID 178418339Butyllithium

Product 1

HCID 131717570HCID 131717570, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

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##

Workup

  1. customThe product resulting from this reaction

Sources & evidence

ORD record
ord-cfdd42175544483b8a5775c6f03652dc
Source dataset
uspto-grants-1992_10
Patent number
US05153680

Reaction notes

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