Isopropyltriphenylphosphonium iodide → Phosphorane, (1-methylethylidene)triphenyl-

HRID 847536Notes

Reaction equation

HRID 847536 reaction equation
C([Li])CCC.[I-].[CH:7]([P+:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:9])[CH3:8]>CCCCCC.O1CCCC1>[C:23]1([P:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:7]([CH3:9])[CH3:8])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 2723783Isopropyltriphenylphosphonium iodideHCID 178418339Butyllithium

Product 1

HCID 140117Phosphorane, (1-methylethylidene)triphenyl-

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of n-butyllithium in hexane was added to a suspension of isopropyltriphenylphosphonium iodide in tetrahydrofuran to obtain a solution of 12.5×10-3M of triphenylisopropylidene phosphorane in tetrahydrofuran and 20 ml of the solution were added to a solution of 1.35 g of the product of Step B in 25 ml of tetrahydrofuran. After stirring at 0° C. for one hour and then at room temperature for one hour, the mixture was diluted with 10 ml of water and was extracted with ether. The extract was dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica to obtain the expected product in a 50 to 60% yield which after crystallization from cyclohexane had a specific rotation of [α]D =-55.5° (c=20.25 in CHCl3).

Sources & evidence

ORD record
ord-2101e605015a4d7b97563dffe2f98fad
Source dataset
uspto-grants-1992_08
Patent number
US05142099

Reaction notes

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