Dimethyl Sulfoxide → 5,5-Bis(4-fluorophenyl)-4-pentenoic acid

HRID 1651215Notes

Reaction equation

HRID 1651215 reaction equation
[H-].[Na+].CS(C)=O.[Cl-].[C:8]([CH2:11][CH2:12][CH2:13][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:10])=[O:9].[F:33][C:34]1[CH:48]=[CH:47][C:37]([C:38]([C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=2)=O)=[CH:36][CH:35]=1>O1CCCC1>[F:33][C:34]1[CH:48]=[CH:47][C:37]([C:38]([C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=2)=[CH:13][CH2:12][CH2:11][C:8]([OH:10])=[O:9])=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 95824,4'-DifluorobenzophenoneHCID 24758Sodium hydrideHCID 21180642(3-Carboxypropyl)(triphenyl)phosphanium chloride

Product 1

HCID 150975595,5-Bis(4-fluorophenyl)-4-pentenoic acidYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction was performed as in Example 87 using sodium hydride (56% dispersion in oil; 9.5 g) dimethylsulfoxide (100 mL), (3-carboxypropyl)triphenylphosphonium chloride (35 g), 4,4'-difluorobenzophenone (23.8 g) and tetrahydrofuran (100 mL). After the usual work up, the crude product was crystallized from ether-hexane to furnish 18.2 g of 5,5-bis(4-fluorophenyl)-4-pentenoic acid, mp 100°-100° C. Anal. Calculated for C17H14F2O2 : C, 70.82; H, 4.89. Found: C, 70.77; H, 5.00.

Workup

  1. customAfter the usual work up, the crude product was crystallized from ether-hexane

Sources & evidence

ORD record
ord-a6744777cace47c7ae3709ff56205c03
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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