Tetrahydrofuran → HCID 70191646, compound

HRID 1740132Notes

Reaction equation

HRID 1740132 reaction equation
[CH3:1][C:2]([O-])([CH3:4])[CH3:3].[K+].[CH:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:11][CH:10]=1)=O.C([O-])(O)=O.[Na+].[CH2:30]1[CH2:34]OC[CH2:31]1>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1>[CH:7](/[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:11][CH:10]=1)=[CH:1]/[C:2]1[CH:4]=[CH:34][CH:30]=[CH:31][CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 15406906HCID 15406906, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 70191646HCID 70191646, compound

Reagents, catalysts & solvents 1

HCID 70671Benzyltriphenylphosphonium chlorideCatalyst

Procedure

9.0 g of benzyltriphenylphosphonium chloride and 2.6 g of KOtBu were stirred at RT for 4 h in 80 ml of anhydrous THF. 3.0 g of 4'-formylbiphenyl-2-sulfonamide were then added and the mixture was stirred at RT for 20 h. 200 ml of a saturated aqueous NaHCO3 solution were added and the mixture was extracted 2 times using 200 ml of EA each time. The organic phase was dried over Na2SO4 and the solvent was removed in vacuo. Chromatography on silica gel using DIP/HEP 1:2 yielded 600 mg of cis-4'-styrylbiphenyl-2-sulfonamide, Rf (DIP/HEP 1:2)=0.25 MS(DCI): 336(M+1)+ and 1.2 g of trans-4'-styrylbiphenyl-2-sulfonamide, Rf (DIP/HEP 1:2)=0.20 MS(DCI): 336(M+1)+

Workup

  1. extractionthe mixture was extracted 2 times
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-24356aa6131745c68f1847f8b15812c0
Source dataset
uspto-grants-1999_10
Patent number
US05968978

Reaction notes

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